Co-reporter:Lewei Zheng, Fei Gao, Chao Yang, Guo-Lin Gao, Yating Zhao, Yuan Gao, and Wujiong Xia
Organic Letters October 6, 2017 Volume 19(Issue 19) pp:
Publication Date(Web):September 18, 2017
DOI:10.1021/acs.orglett.7b02251
The development of photoredox reactions of 1,3-dipolar cycloaddition of nitrones with alkenes is reported. It offers an efficient synthetic method to obtain isoxazolidine derivatives under mild conditions in synthetically useful yields. The nitrones are cyclized with oxidizable styrenes and aliphatic alkenes via a polar radical crossover cycloaddition reaction through photocatalytic reaction without additives. In addition, bis(indole)methanes can also be prepared through this method.
Co-reporter:Ming Chen, Xinxin Zhao, Chao Yang, and Wujiong Xia
Organic Letters July 21, 2017 Volume 19(Issue 14) pp:3807-3807
Publication Date(Web):July 11, 2017
DOI:10.1021/acs.orglett.7b01677
The first visible-light-mediated radical–radical cross-coupling strategy that enables the direct arylation of carbonyl/iminyl derivatives in the presence of Et3N has been realized. Such an atom-economical protocol furnishes a broad scope of arylation products such as secondary/tertiary alcohols and amines via a PCET process that facilitates the challenging reduction of C═X (X = O, N). Mechanistic investigation indicates two photocatalytic redox cycles were involved in the process, and Et3N was proved to serve as a dual reductant and proton donor. Moreover, the isolated byproducts and controlled experiments could be considered as powerful supporting evidence for our hypothesis.
Co-reporter:Binbin Huang, Yating Zhao, Chao Yang, Yuan Gao, and Wujiong Xia
Organic Letters July 21, 2017 Volume 19(Issue 14) pp:3799-3799
Publication Date(Web):June 29, 2017
DOI:10.1021/acs.orglett.7b01427
A mild, metal-free, and absolutely para-selective bromination of aniline derivatives has been developed in excellent yields, wherein the organic dye Eosin Y is employed as the bromine source in company with Selectfluor. Neither air nor moisture sensitive, this facile reaction proceeds smoothly at room temperature and completes within a short time. Mechanistic studies indicate a radical pathway; therefore, the existence of an in situ generated brominating reagent, “Selectbrom”, is postulated, which may reasonably account for the unique regioselectivity for the para-bromination of N-acyl- as well as N-sulfonylanilines.
Co-reporter:Qiang Liu, Junlei Wang, Dazhi Li, Guo-Lin Gao, Chao Yang, Yuan Gao, and Wujiong Xia
The Journal of Organic Chemistry August 4, 2017 Volume 82(Issue 15) pp:7856-7856
Publication Date(Web):July 12, 2017
DOI:10.1021/acs.joc.7b01055
The photolysis of substituted o-divinylbenzenes promotes a one-step and metal-free conversion to oxatricycles at room temperature. Irradiation o-divinylbenzenes results in an pericyclic reaction to form cyclic o-quinodiemthane intermediates, which subsequently undergo intramolecular oxa-[4+2] cycloaddition to form oxacyclic derivatives.
Co-reporter:Ming Chen;Xinxin Zhao;Chao Yang;Yanpei Wang
RSC Advances (2011-Present) 2017 vol. 7(Issue 20) pp:12022-12026
Publication Date(Web):2017/02/16
DOI:10.1039/C7RA00193B
Reported herein is further insight into the photochemical behaviour of 3-aryl-N-(arylsulfonyl)-propiolamides, which provides a straightforward way to access meaningful phenanthrenes. Mechanistic investigation indicated that aryl migration, C–C coupling, 1,3-hydrogen shift, desulfonylation and elimination were involved in the process. Moreover, this protocol allowed for scale-up using a flow reactor.
Co-reporter:Qiang LiuJunlei Wang, Dazhi Li, Chao Yang, Wujiong Xia
The Journal of Organic Chemistry 2017 Volume 82(Issue 3) pp:
Publication Date(Web):January 5, 2017
DOI:10.1021/acs.joc.6b02547
A novel and efficient method for the synthesis of highly substituted benzobicyclo[2.2.2]octane skeletons has been explored. Under UV-light irradiation, o-divinylbenzenes underwent a pericyclic reaction to form the cyclic o-quinodimethane intermediates which were subsequently reacted with olefins through [4+2] addition to construct the benzobicyclo[2.2.2]octane skeletons in mild conditions. Gram scale reactions demonstrated the synthetic potential application of this protocol.
Co-reporter:Fei Gao;Jiu-Tao Wang;Lin-Lin Liu;Na Ma;Chao Yang;Yuan Gao
Chemical Communications 2017 vol. 53(Issue 61) pp:8533-8536
Publication Date(Web):2017/07/27
DOI:10.1039/C7CC04813K
An efficient strategy for the easy access to carbonylated heteroaromatic compounds has been developed via a visible-light-promoted intramolecular decarboxylative cyclization reaction of o-alkynylated carboxylic acids. This method is characterized by its benign conditions and the tolerance to a wide range of functionalities.
Co-reporter:Guo-Lin Gao;Chao Yang
Chemical Communications 2017 vol. 53(Issue 6) pp:1041-1044
Publication Date(Web):2017/01/17
DOI:10.1039/C6CC08975E
The protocol presented here is a new strategy for visible light induced C–H trifluoromethylation at C4 of benzimidazoles using Togni's reagent in the presence of fac-Ir(ppy)3. Its advantages are its operational simplicity, mild reaction conditions, low catalyst loading and wide substrate scope in which electron-withdrawing, electron-donating groups and different protecting groups are tolerated.
Co-reporter:Wei Li;Guolin Gao;Yuan Gao;Chao Yang
Chemical Communications 2017 vol. 53(Issue 38) pp:5291-5293
Publication Date(Web):2017/05/09
DOI:10.1039/C7CC01868A
A novel pathway for direct conversion of benzylsilanes to phenols by oxidation with Na2S2O8 and oxygen is efficiently developed under mild and neutral conditions. The reaction shows good functional group tolerance to afford phenols in moderate yields. The possible mechanism is proposed based on the isotopic labeling trials.
Co-reporter:Junlei Wang;Yating Zhao;Han Gao;Guo-Lin Gao; Dr. Chao Yang; Dr. Wujiong Xia
Asian Journal of Organic Chemistry 2017 Volume 6(Issue 10) pp:1402-1407
Publication Date(Web):2017/10/01
DOI:10.1002/ajoc.201700242
AbstractThe direct cross-dehydrogenative coupling reactions of 2-naphthylamine/2-naphthol derivatives with aniline/phenol derivatives for the preparation of nonsymmetrical atropisomeric biaryl compounds, especially BINOL-type biaryls, using a photocatalyst with irradiation under blue LEDs at room temperature, are described. This protocol provides efficient and simple access to nonsymmetrical atropisomeric biaryls in good yields, which are often found in natural products and are useful for materials chemistry.
Co-reporter:Yating Zhao, Binbin Huang, Chao Yang, and Wujiong Xia
Organic Letters 2016 Volume 18(Issue 14) pp:3326-3329
Publication Date(Web):July 1, 2016
DOI:10.1021/acs.orglett.6b01371
A transition-metal-free approach was disclosed for intermolecular aryl C–N bonds formation between phenols and cyclic anilines via cross-dehydrogenative coupling (CDC) amination that was mediated by visible light, wherein K2S2O8 served as an external oxidant. The salient features of this protocol include circumventing the requirement for prefunctionalized starting materials and achieving single regioselectivity of amination adducts at room temperature.
Co-reporter:Ming Chen, Chao Yang, Yanpei Wang, Dazhi Li, and Wujiong Xia
Organic Letters 2016 Volume 18(Issue 9) pp:2280-2283
Publication Date(Web):April 26, 2016
DOI:10.1021/acs.orglett.6b00878
A novel photochemical approach for the synthesis of phenanthrene derivatives from linear 3-aryl-N-(arylsulfonyl) propiolamides via a tandem radical Smiles rearrangement/C–S bonding/Mallory reaction is disclosed. The control experiment results and isolation of the key intermediates give further insight into the reaction mechanism. Gram scale reaction using a flow reactor demonstrated the synthetic potential applications of our protocol.
Co-reporter:Fei Gao, Chao Yang, Na Ma, Guo-Lin Gao, Dazhi Li, and Wujiong Xia
Organic Letters 2016 Volume 18(Issue 3) pp:600-603
Publication Date(Web):January 20, 2016
DOI:10.1021/acs.orglett.5b03662
A photocatalytic process for 1,7-enyne bicyclizations with α-bromo diethyl malonate has been established via synergistic domino bicyclizations. This protocol provides an efficient and practical method for the synthesis of various cyclopenta[c]quinolines and benzo[j]phenanthridines under operational simplicity and mild reaction conditions.
Co-reporter:Yating Zhao, Binbin Huang, Chao Yang, Qingqing Chen, and Wujiong Xia
Organic Letters 2016 Volume 18(Issue 21) pp:5572-5575
Publication Date(Web):October 18, 2016
DOI:10.1021/acs.orglett.6b02811
A photoredox catalytic route to carbamates enabled by visible irradiation (or simply sunlight) has been developed. This process leads to a novel approach to the construction of heterocyclic rings wherein the amide or ester motifs of carbamates were assembled from three isolated components. Large-scale experiments were realized by employing continuous flow techniques, and reuse of photocatalyst demonstrated the green and sustainable aspects of this method.
Co-reporter:Bing Li, Dan Fan, Chao Yang and Wujiong Xia
Organic & Biomolecular Chemistry 2016 vol. 14(Issue 23) pp:5293-5297
Publication Date(Web):11 May 2016
DOI:10.1039/C6OB00912C
A metal-free and cost-effective protocol for UV light-mediated difunctionalization of alkenes with CF3SO2Na was developed. This strategy realized the direct formation of Csp3–CF3 and C–C bonds through a proposed tandem radical cyclization process, which produced a variety of phenanthrene and anthrone derivatives in moderate yields.
Co-reporter:Liyan Feng, Hang Yan, Chao Yang, Dafa Chen, and Wujiong Xia
The Journal of Organic Chemistry 2016 Volume 81(Issue 16) pp:7008-7022
Publication Date(Web):May 11, 2016
DOI:10.1021/acs.joc.6b00436
In this article, a photoredox protocol for the synthesis of furans via oxidative coupling of olefin generated in situ from cyclopropyl ketones with ketonic oxygen atom is presented. Moreover, bromination of furans in the presence of overstoichiometric oxidant has been achieved with high regioselectivity.
Co-reporter:Dan Wang;Yating Zhao;Chao Yang
Science China Chemistry 2016 Volume 59( Issue 2) pp:190-194
Publication Date(Web):2016 February
DOI:10.1007/s11426-015-5530-7
A visible light-mediated approach for the preparation of α-bromo-α,β-unsaturated ketones and aldehydes was developed. In comparison to traditional methods that generally take two steps to afford the above compounds, this protocol was highlighted by its operational simplicity, avoiding using hazardous bromine and mild reaction conditions.
Co-reporter:Lewei Zheng, Hongli Huang, Chao Yang, and Wujiong Xia
Organic Letters 2015 Volume 17(Issue 4) pp:1034-1037
Publication Date(Web):February 11, 2015
DOI:10.1021/acs.orglett.5b00144
UV light-mediated difunctionalization of alkenes through an aroyl radical addition/1,4-/1,2-aryl shift has been described. The resulted aroyl radical from a photocleavage reaction added to acrylamide compounds followed by cyclization led to the formation of oxindoles, whereas the addition to cinnamic amides aroused a unique 1,4-aryl shift reaction. Furthermore, the difunctionalization of alkenes of prop-2-en-1-ols was also achieved through aroyl radical addition and a sequential 1,2-aryl shift cascade reaction.
Co-reporter:Hong-Li Huang, Hang Yan, Chao Yang and Wujiong Xia
Chemical Communications 2015 vol. 51(Issue 23) pp:4910-4913
Publication Date(Web):13 Feb 2015
DOI:10.1039/C4CC10321A
A photocatalytic process for selective arylalkylation of allylic alcohols with α-bromo diethyl malonate has been developed. The reaction provided a straightforward approach to synthesize α-aryl-β-alkylated ketones via unique 1,2-aryl migration. The procedure is highlighted by its operational simplicity and mild reaction conditions.
Co-reporter:Run Lin, Hongnan Sun, Chao Yang, Wenbo Shen and Wujiong Xia
Chemical Communications 2015 vol. 51(Issue 2) pp:399-401
Publication Date(Web):04 Nov 2014
DOI:10.1039/C4CC08221D
The difunctionalization of electron-enriched styrenes for the synthesis of substituted tetrahydrofurans and tetrahydropyrans in the presence of photoredox catalysts is described. The procedure is highlighted by its operational simplicity, low catalyst loadings (1 mol%), excellent stereoselectivity and mild reaction conditions.
Co-reporter:Fei Gao, Chao Yang, Guo-Lin Gao, Lewei Zheng, and Wujiong Xia
Organic Letters 2015 Volume 17(Issue 14) pp:3478-3481
Publication Date(Web):July 1, 2015
DOI:10.1021/acs.orglett.5b01530
The visible-light induced trifluoromethylation of N-arylcinnamamides with Togni’s reagent has been explored. This method allows for an efficient and practical synthesis of a variety of CF3-containing dihydroquinolin-2(1H)-ones and 1-azasporo[4.5]decanes bearing various functional groups under mild conditions.
Co-reporter:Lewei Zheng, Chao Yang, ZhaoZhong Xu, Fei Gao, and Wujiong Xia
The Journal of Organic Chemistry 2015 Volume 80(Issue 11) pp:5730-5736
Publication Date(Web):May 8, 2015
DOI:10.1021/acs.joc.5b00677
A novel visible-light-induced trifluoromethylarylation/1,4-aryl shift/desulfonylation cascade reaction using CF3SO2Cl as CF3 source was described. The protocol provides an efficient approach for the synthesis of α-aryl-β-trifluoromethyl amides and/or CF3-containing oxindoles as well as the isoquinolinediones under benign conditions.
Co-reporter:Hongnan Sun;Chao Yang;Run Lin
Advanced Synthesis & Catalysis 2014 Volume 356( Issue 13) pp:2775-2780
Publication Date(Web):
DOI:10.1002/adsc.201400476
Co-reporter:Liyan Zhao, Xiaoming Chen, Fang Guo, Baoquan Gou, Chao Yang, Wujiong Xia
Journal of Luminescence 2014 Volume 145() pp:486-491
Publication Date(Web):January 2014
DOI:10.1016/j.jlumin.2013.08.012
•Stimulations of Na+ and Zn2+ cause response molecule to express ‘AND’ logic function.•The output is the detectable fluorescence signal.•The spectrum changes were originated from the photoinduced electron transfer.•Response molecule exhibit fluorosolvatochromism.An N-salicylidenaniline (SA), compound 1 with 15-crown-5 moiety, was synthesized. Coordinations with Na+ or/and Zn2+ induced obvious changes in fluorescence spectra. When the solvent changed from ethanol to acetonitrile, compound 1 and its complexes exhibited noticeable fluorosolvatochromism. However, the spectral changes all could express the AND logic function in these two solvents. The changes in fluorescence spectra were interpreted as photoinduced electron transfer (PET) and charge transfer transition (CT) mechanisms.
Co-reporter:Manling Ma;Feixue Xue;Chao Yang
Chinese Journal of Chemistry 2014 Volume 32( Issue 4) pp:307-312
Publication Date(Web):
DOI:10.1002/cjoc.201300893
Abstract
The photochemical behavior of bicyclo[2.1.1]hexyl derivatives was investigated by irradiation with a 450 W medium-pressure mercury lamp in acetonitrile solution. The irradiation of methyl bicyclo[2.1.1]hexane-5-carbonylbenzoate (1a) led to both Norrish type II cyclization and cleavage products with a molar ratio of 1:2.2, whereas the irradiation of methyl 5-methylbicyclo[2.1.1]hexane-5-carbonylbenzoate (1b) afforded the only Norrish/Yang photocyclization compound as the sole product. Such results were illustrated by several geometric parameters for Norrish/Yang photoreaction as ϕ1, ϕ4 and β obtained from the crystal structures. Furthermore, asymmetric photochemical studies using ionic chiral auxiliary technique were also conducted in the solid state.
Co-reporter:Liyan Zhao, Wujiong Xia, Chao Yang
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2014 Volume 117() pp:397-401
Publication Date(Web):3 January 2014
DOI:10.1016/j.saa.2013.08.009
•A fluorescent 1:2 demultiplexer was expressed.•A fluorescent half-subtractor were expressed.•The spectrum changes were originated from the photoinduced electron transfer.In moist chloroform solution, the ultraviolet light irradiation would cause N-salicylidene-3-aminopyridine (L) to hydrolyze into salicylaldehyde and 3-aminopyridine. To consider an optical signal (UV light) and a chemical signal (Zn2+) as inputs, the luminescence signals as outputs, the logic behavior of compound L was investigated. Interestingly, excited by two different wavelengths lights, two sharp distinct fluorescent spectra were collected. Consequently, a fluorescent 1:2 demultiplexer and a fluorescent half-subtractor were respectively expressed.Based on the hydrolysis, a simple molecule has implemented the important demultiplexer and half-subtractor.
Co-reporter:Yunfeng Qiu, Hongnan Sun, Zhuo Ma, Wujiong Xia
Journal of Molecular Catalysis A: Chemical 2014 Volume 392() pp:76-82
Publication Date(Web):October 2014
DOI:10.1016/j.molcata.2014.04.031
•Preparation of cerium(III) trislaurylsulfonate (Ce(LS)3) and characterization by SEM, SEM-EDX, XRD, NMR, FT-IR, TG, and elemental analysis.•Extend the application of Ce(LS)3 in one-pot Biginelli reaction and esterification under neat condition.•Ce(LS)3 is an efficient, air stable and reusable micro-reactor.Cerium(III) trislaurylsulfonate (Ce(LS)3), a Lewis acid and surfactant combined catalyst, was prepared and characterized by SEM, SEM-EDX, XRD, NMR, FT-IR, TG, and elemental analysis. Ce(LS)3 was found to be stable and efficient to catalyze one-pot Biginelli and solvent-free esterification reactions. Furthermore, Ce(LS)3 is easy to recycle after reaction by pouring into cold water and filtration. Present work will shed deep insight into the understanding of the catalytic nature of LASCs, and extend its application in important organic transformations.Cerium(III) trislaurylsulfonate (Ce(LS)3), a Lewis acid and surfactant combined catalyst, was prepared and characterized by SEM, SEM-EDX, XRD, NMR, FT-IR, TG, and elemental analysis. Ce(LS)3 was found to be stable and efficient to catalyze one-pot Biginelli and solvent-free esterification reactions. Furthermore, Ce(LS)3 is easy to recycle after reaction by pouring into cold water and filtration. Present work will shed deep insight into the understanding of the catalytic nature of LASCs, and extend its application in important organic transformations.
Co-reporter:Qiang Liu, Jiang Meng, Yang Liu, Chao Yang, and Wujiong Xia
The Journal of Organic Chemistry 2014 Volume 79(Issue 17) pp:8143-8155
Publication Date(Web):August 18, 2014
DOI:10.1021/jo5013465
Irradiation of ortho-formyl dienes with UV light led to benzobicycloheptanones in high yields and chemoselectivities via a photogenerated ketene methide/Diels–Alder cascade reaction. The reaction mechanism was proposed to be a [1,5]-H shift process rather than a radical pathway based on control experiments. DFT calculations indicate that the energy of transition states is responsible for the high chemoselectivity observed in this protocol.
Co-reporter:Hongnan Sun, Chao Yang, Fei Gao, Zhe Li, and Wujiong Xia
Organic Letters 2013 Volume 15(Issue 3) pp:624-627
Publication Date(Web):January 11, 2013
DOI:10.1021/ol303437m
The visible-light mediated oxidative C–C bond cleavage of aldehydes has been achieved in good yields at ambient temperature and open to air using Ru(bpy)3Cl2 (bpy = 2,2′-bipyridine) as the photoredox catalyst. Moreover, we further demonstrated the application in a tandem Michael/oxidative C–C bond cleavage reaction.
Co-reporter:Qian Chen, Chao Chen, Fang Guo and Wujiong Xia
Chemical Communications 2013 vol. 49(Issue 57) pp:6433-6435
Publication Date(Web):30 May 2013
DOI:10.1039/C3CC42673D
Chiral N-tert-butylsulfinyl vinyl aziridine ligands prepared from a readily available (R)-tert-butanesulfinamide have been applied in the rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to cyclic enones, which gives high yields and excellent enantioselectivities.
Co-reporter:Lin Guo, Chao Yang, Lewei Zheng and Wujiong Xia
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 35) pp:5787-5792
Publication Date(Web):10 Jul 2013
DOI:10.1039/C3OB41245H
A novel and simple procedure was developed for the regioselective synthesis of α-bromo (di)ketones from electron-rich epoxides via visible light photoredox catalysis. Through optimization of solvent and light source, the reaction can be rapidly achieved under mild conditions. Moreover, the possible reaction mechanism was proposed and further supported by control experiments.
Co-reporter:Lei Shi and Wujiong Xia
Chemical Society Reviews 2012 vol. 41(Issue 23) pp:7687-7697
Publication Date(Web):06 Aug 2012
DOI:10.1039/C2CS35203F
The functionalization of C–H bonds and the visible light photoredox catalysis represent two prominent challenges in organic chemistry. In this regard, the combination of visible-light catalysis and C–H bond functionalization adjacent to a tertiary amine has been successfully developed in the past three years. In this tutorial review, we aim to give a brief overview of this issue and state the main results obtained in the reactions.
Co-reporter:Guolei Zhao, Chao Yang, Hongnan Sun, Run Lin, and Wujiong Xia
Organic Letters 2012 Volume 14(Issue 3) pp:776-779
Publication Date(Web):January 20, 2012
DOI:10.1021/ol203314y
An efficient approach to construct an enantiomerically pure cyclobutane skeleton by means of the chiral auxiliary induced [2 + 2] photoaddition reactions has been described. This asymmetric photoreaction exhibited high diastereoselectivity and provided the photoadducts in excellent yields.
Co-reporter:Yutian Shao, Chao Yang, Weijun Gui, Yang Liu and Wujiong Xia
Chemical Communications 2012 vol. 48(Issue 29) pp:3560-3562
Publication Date(Web):17 Feb 2012
DOI:10.1039/C2CC17960A
Irradiation of terminal aromatic γ,δ-epoxy ketones with a 450 W UV lamp led to Norrish type II cyclization/semi-pinacol rearrangement cascade reaction which formed the benzocyclobutanones containing a full-carbon quaternary center, whereas irradiation of substituted aromatic γ,δ-epoxy ketones led to the indanones through a photochemical epoxy rearrangement and 1,5-biradicals cyclization tandem reaction.
Co-reporter:Guolei Zhao, Chao Yang, Lin Guo, Hongnan Sun, Chao Chen and Wujiong Xia
Chemical Communications 2012 vol. 48(Issue 17) pp:2337-2339
Publication Date(Web):09 Jan 2012
DOI:10.1039/C2CC17130A
An efficient methodology for the functionalization of sp3 C–H bond adjacent to nitrogen has been developed utilizing visible light-induced photoredox catalysis. Through optimization of solvent and light source, the reaction can be rapidly achieved to provide the desired product under mild reaction conditions.
Co-reporter:Manling Ma;Chao Yang;Bing Li;Yutian Shao;Guolei Zhao
Chinese Journal of Chemistry 2012 Volume 30( Issue 1) pp:91-95
Publication Date(Web):
DOI:10.1002/cjoc.201100083
Abstract
The first example of the p-orbital overlap controlled enantioselectivity of Norrish type II photocyclization reaction was described. Irradiation of 5-methyl bicyclo[1.1.1]pentanyl ketone with UV in the solid state as well as in the acetonitrile solution afforded the Norrish/Yang photocyclization compound as the sole product. Solid-state asymmetric photochemical studies using ionic chiral auxiliary technique led to the enantioselectivity as high as 60%. The results were rationalized by X-ray single crystal structure.
Co-reporter:Ankun Zhou;Lei Wu;Dazhi Li;Qingqing Chen;Xiao Zhang
Chinese Journal of Chemistry 2012 Volume 30( Issue 8) pp:1862-1866
Publication Date(Web):
DOI:10.1002/cjoc.201200387
Abstract
A novel method for the synthesis of esters via reductive coupling of N-tosylhydrazones with carboxylic acids under metal-free conditions has been developed. Various functional groups were found to be tolerable under the reaction conditions to afford low to good yields.
Co-reporter:Manling Ma, Wei Feng, Fang Guo, Chao Yang, Wujiong Xia
Tetrahedron 2012 68(43) pp: 8875-8879
Publication Date(Web):
DOI:10.1016/j.tet.2012.08.040
Co-reporter:Guolei Zhao, Chao Yang, Lin Guo, Hongnan Sun, Run Lin, and Wujiong Xia
The Journal of Organic Chemistry 2012 Volume 77(Issue 14) pp:6302-6306
Publication Date(Web):June 25, 2012
DOI:10.1021/jo300796j
The reductive coupling and cyclization of chalcones to generate cyclopentanol derivatives in up to 84% yield by visible light photoredox catalysis is described. This reaction involves radical anion homocoupling, monoprotonation, and intramolecular cyclization cascade.
Co-reporter:Baoquan Gou, Dazhi Li, Chao Yang, Wujiong Xia, Yali Li, Xiaoming Chen
Journal of Photochemistry and Photobiology A: Chemistry 2012 Volume 233() pp:46-49
Publication Date(Web):1 April 2012
DOI:10.1016/j.jphotochem.2012.02.008
Metal free conversion of aryl CO to CC bond through a photochemical rearrangement/oxidation cascade reaction is described. Irradiation of O-acetyl aryloxy benzene derivatives in benzene solution undergoes a unique photochemical rearrangement reaction to afford the ketal compounds, which are sequentially oxidized by 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) to yield the diketone compounds.Graphical abstractHighlights► The direct conversion of aromatic CO to CC without metallic catalyst was developed. ► The conversion could be realized by a hν activation/TEMPO oxidation cascade reaction. ► The photochemical approach could compensate the Friedal–Crafts acylation reaction. ► The research enriches the application of photochemical reactions in organic synthesis.
Co-reporter:Liyan Zhao, Wujiong Xia, Baoquan Gou, Yu Lu, Chao Yang, Dazhi Li
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2012 Volume 95() pp:199-203
Publication Date(Web):September 2012
DOI:10.1016/j.saa.2012.04.016
An N-salicylidenaniline (SA), compound 1 with 15-crown-5 moiety, was synthesized. The time-dependent NMR was used to track its photochromic process. The experimental results showed that ultraviolet irradiation would lead compound 1 to decompose into the corresponding salicylaldehyde and amine in chloroform solution, instead of experiencing a photochromic process. By the same method, the reported photochromic results of other SAs were also corrected.Graphical abstractUltraviolet irradiation would lead N-salicylidenanilines (SAs) to decompose into the corresponding salicylaldehyde and amine in chloroform solution, instead of experiencing a photochromic process.Highlights► N-salicylidenaniline (SA) was decomposed in chloroform solution, not in photochromism. ► The results of other SAs reported in previous papers were also corrected. ► Chloroform is not appropriate solvent for investigating the photochromism of SAs.
Co-reporter:Wujiong Xia, Yutian Shao, Weijun Gui and Chao Yang
Chemical Communications 2011 vol. 47(Issue 39) pp:11098-11100
Publication Date(Web):12 Sep 2011
DOI:10.1039/C1CC14269K
A novel and convenient approach to the synthesis of polysubstituted isochromanones is described. Irradiation of 2-formyl phenylalkeno-derivatives with UV light in benzene solution afforded the corresponding products in up to 98% yield. The possible reaction mechanism is proposed and further supported by the isotopic experiments.
Co-reporter:Xiao Zhang, Zhihui Yi, Liyan Zhao, Qian Chen, Xianmo Gu, Jiqing Xu, Xiaolin Wang, Chao Yang, Xianzhu Xu and Wujiong Xia
Dalton Transactions 2009 (Issue 42) pp:9198-9206
Publication Date(Web):03 Sep 2009
DOI:10.1039/B906313G
Three supramolecular architectures based on α-Keggin-type polyoxometalates have been synthesized hydrothermally, and their structures have been characterized by elemental analyses, infrared (IR) spectroscopy, X-ray photoelectron spectroscopy (XPS) and single crystal X-ray diffraction structure analyses. [Ni(enMe)2(H2O)2]2[Ni(enMe)2PWVI9WV3O40]·H2O (1) (enMe = 1,2′-propanediamine) exhibits a novel 2-D supramolecular sinusoidal layer through the interactions between transition metal complexes and 1-D covalent chains which are constructed from α-Keggin units bridged by transition metal complexes. [Ni(enMe)2]4{[Ni(enMe)2][Ni(enMe)2(H2O)AsWVI6WV4VIV4O42]2}·6H2O (2), representing a 3-D supramolecular framework with 1-D channels, contains the first example of a tungstate dimer with inorganic–organic composite surfaces built up from [Ni(enMe)2]2+ cation bridges and bi-capped α-Keggin polyoxometalate building blocks supporting the transition metal complex. [Ni(enMe)2]4{[Ni(enMe)2][Ni(enMe)2(H2O)AsMoVI4MoV4VIV8O44]2}·8H2O (3), showing a 3-D supramolecular framework with 1-D channels, contains the first example of a molybdoarsenate dimer formed by [Ni(enMe)2]2+ cations bridging two neighboring tetra-capped α-Keggin-based molybdates that support the transition metal complex [Ni(enMe)2H2O]. The topological networks of the supramolecular frameworks of 2 and 3 are analogous. Crystal structural analysis reveals that the dimensionality and the organization of polyoxometalate building units in the solid state can be tuned by the steric hindrances of the polyanions. Both 2 and 3 exhibit intensive photoluminescence.
Co-reporter:Guolei Zhao, Chao Yang, Qian Chen, Jing Jin, Xiao Zhang, Liyan Zhao, Wujiong Xia
Tetrahedron 2009 65(48) pp: 9952-9955
Publication Date(Web):
DOI:10.1016/j.tet.2009.10.011
Co-reporter:Chao Yang Dr. Dr.
Chemistry – An Asian Journal 2009 Volume 4( Issue 12) pp:1774-1784
Publication Date(Web):
DOI:10.1002/asia.200900249
Abstract
The ionic chiral auxiliary approach to asymmetric photochemical synthesis discovered by the Scheffer group has been successfully applied to many reactions in the solid state. Enantiomeric excesses of up to 99 % were obtained using this method. After a brief introduction of absolute asymmetric synthesis, chirally modified zeolites and host–guest assemblies in asymmetric photochemistry, the bulk of this review will summarize and discuss the application of the solid state ionic chiral auxiliary technique to the Norrish type II reaction, the di-π-methane photorearrangement, and to a novel retro-Claisen photorearrangement.
Co-reporter:Lin Guo, Chao Yang, Lewei Zheng and Wujiong Xia
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 35) pp:NaN5792-5792
Publication Date(Web):2013/07/10
DOI:10.1039/C3OB41245H
A novel and simple procedure was developed for the regioselective synthesis of α-bromo (di)ketones from electron-rich epoxides via visible light photoredox catalysis. Through optimization of solvent and light source, the reaction can be rapidly achieved under mild conditions. Moreover, the possible reaction mechanism was proposed and further supported by control experiments.
Co-reporter:Run Lin, Hongnan Sun, Chao Yang, Wenbo Shen and Wujiong Xia
Chemical Communications 2015 - vol. 51(Issue 2) pp:NaN401-401
Publication Date(Web):2014/11/04
DOI:10.1039/C4CC08221D
The difunctionalization of electron-enriched styrenes for the synthesis of substituted tetrahydrofurans and tetrahydropyrans in the presence of photoredox catalysts is described. The procedure is highlighted by its operational simplicity, low catalyst loadings (1 mol%), excellent stereoselectivity and mild reaction conditions.
Co-reporter:Yutian Shao, Chao Yang, Weijun Gui, Yang Liu and Wujiong Xia
Chemical Communications 2012 - vol. 48(Issue 29) pp:NaN3562-3562
Publication Date(Web):2012/02/17
DOI:10.1039/C2CC17960A
Irradiation of terminal aromatic γ,δ-epoxy ketones with a 450 W UV lamp led to Norrish type II cyclization/semi-pinacol rearrangement cascade reaction which formed the benzocyclobutanones containing a full-carbon quaternary center, whereas irradiation of substituted aromatic γ,δ-epoxy ketones led to the indanones through a photochemical epoxy rearrangement and 1,5-biradicals cyclization tandem reaction.
Co-reporter:Wujiong Xia, Yutian Shao, Weijun Gui and Chao Yang
Chemical Communications 2011 - vol. 47(Issue 39) pp:NaN11100-11100
Publication Date(Web):2011/09/12
DOI:10.1039/C1CC14269K
A novel and convenient approach to the synthesis of polysubstituted isochromanones is described. Irradiation of 2-formyl phenylalkeno-derivatives with UV light in benzene solution afforded the corresponding products in up to 98% yield. The possible reaction mechanism is proposed and further supported by the isotopic experiments.
Co-reporter:Qian Chen, Chao Chen, Fang Guo and Wujiong Xia
Chemical Communications 2013 - vol. 49(Issue 57) pp:NaN6435-6435
Publication Date(Web):2013/05/30
DOI:10.1039/C3CC42673D
Chiral N-tert-butylsulfinyl vinyl aziridine ligands prepared from a readily available (R)-tert-butanesulfinamide have been applied in the rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to cyclic enones, which gives high yields and excellent enantioselectivities.
Co-reporter:Hong-Li Huang, Hang Yan, Chao Yang and Wujiong Xia
Chemical Communications 2015 - vol. 51(Issue 23) pp:NaN4913-4913
Publication Date(Web):2015/02/13
DOI:10.1039/C4CC10321A
A photocatalytic process for selective arylalkylation of allylic alcohols with α-bromo diethyl malonate has been developed. The reaction provided a straightforward approach to synthesize α-aryl-β-alkylated ketones via unique 1,2-aryl migration. The procedure is highlighted by its operational simplicity and mild reaction conditions.
Co-reporter:Guolei Zhao, Chao Yang, Lin Guo, Hongnan Sun, Chao Chen and Wujiong Xia
Chemical Communications 2012 - vol. 48(Issue 17) pp:NaN2339-2339
Publication Date(Web):2012/01/09
DOI:10.1039/C2CC17130A
An efficient methodology for the functionalization of sp3 C–H bond adjacent to nitrogen has been developed utilizing visible light-induced photoredox catalysis. Through optimization of solvent and light source, the reaction can be rapidly achieved to provide the desired product under mild reaction conditions.
Co-reporter:Bing Li, Dan Fan, Chao Yang and Wujiong Xia
Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 23) pp:NaN5297-5297
Publication Date(Web):2016/05/11
DOI:10.1039/C6OB00912C
A metal-free and cost-effective protocol for UV light-mediated difunctionalization of alkenes with CF3SO2Na was developed. This strategy realized the direct formation of Csp3–CF3 and C–C bonds through a proposed tandem radical cyclization process, which produced a variety of phenanthrene and anthrone derivatives in moderate yields.
Co-reporter:Xiao Zhang, Zhihui Yi, Liyan Zhao, Qian Chen, Xianmo Gu, Jiqing Xu, Xiaolin Wang, Chao Yang, Xianzhu Xu and Wujiong Xia
Dalton Transactions 2009(Issue 42) pp:NaN9206-9206
Publication Date(Web):2009/09/03
DOI:10.1039/B906313G
Three supramolecular architectures based on α-Keggin-type polyoxometalates have been synthesized hydrothermally, and their structures have been characterized by elemental analyses, infrared (IR) spectroscopy, X-ray photoelectron spectroscopy (XPS) and single crystal X-ray diffraction structure analyses. [Ni(enMe)2(H2O)2]2[Ni(enMe)2PWVI9WV3O40]·H2O (1) (enMe = 1,2′-propanediamine) exhibits a novel 2-D supramolecular sinusoidal layer through the interactions between transition metal complexes and 1-D covalent chains which are constructed from α-Keggin units bridged by transition metal complexes. [Ni(enMe)2]4{[Ni(enMe)2][Ni(enMe)2(H2O)AsWVI6WV4VIV4O42]2}·6H2O (2), representing a 3-D supramolecular framework with 1-D channels, contains the first example of a tungstate dimer with inorganic–organic composite surfaces built up from [Ni(enMe)2]2+ cation bridges and bi-capped α-Keggin polyoxometalate building blocks supporting the transition metal complex. [Ni(enMe)2]4{[Ni(enMe)2][Ni(enMe)2(H2O)AsMoVI4MoV4VIV8O44]2}·8H2O (3), showing a 3-D supramolecular framework with 1-D channels, contains the first example of a molybdoarsenate dimer formed by [Ni(enMe)2]2+ cations bridging two neighboring tetra-capped α-Keggin-based molybdates that support the transition metal complex [Ni(enMe)2H2O]. The topological networks of the supramolecular frameworks of 2 and 3 are analogous. Crystal structural analysis reveals that the dimensionality and the organization of polyoxometalate building units in the solid state can be tuned by the steric hindrances of the polyanions. Both 2 and 3 exhibit intensive photoluminescence.
Co-reporter:Lei Shi and Wujiong Xia
Chemical Society Reviews 2012 - vol. 41(Issue 23) pp:NaN7697-7697
Publication Date(Web):2012/08/06
DOI:10.1039/C2CS35203F
The functionalization of C–H bonds and the visible light photoredox catalysis represent two prominent challenges in organic chemistry. In this regard, the combination of visible-light catalysis and C–H bond functionalization adjacent to a tertiary amine has been successfully developed in the past three years. In this tutorial review, we aim to give a brief overview of this issue and state the main results obtained in the reactions.
Co-reporter:Wei Li, Guolin Gao, Yuan Gao, Chao Yang and Wujiong Xia
Chemical Communications 2017 - vol. 53(Issue 38) pp:NaN5293-5293
Publication Date(Web):2017/04/18
DOI:10.1039/C7CC01868A
A novel pathway for direct conversion of benzylsilanes to phenols by oxidation with Na2S2O8 and oxygen is efficiently developed under mild and neutral conditions. The reaction shows good functional group tolerance to afford phenols in moderate yields. The possible mechanism is proposed based on the isotopic labeling trials.
Co-reporter:Fei Gao, Jiu-Tao Wang, Lin-Lin Liu, Na Ma, Chao Yang, Yuan Gao and Wujiong Xia
Chemical Communications 2017 - vol. 53(Issue 61) pp:NaN8536-8536
Publication Date(Web):2017/07/06
DOI:10.1039/C7CC04813K
An efficient strategy for the easy access to carbonylated heteroaromatic compounds has been developed via a visible-light-promoted intramolecular decarboxylative cyclization reaction of o-alkynylated carboxylic acids. This method is characterized by its benign conditions and the tolerance to a wide range of functionalities.
Co-reporter:Guo-Lin Gao, Chao Yang and Wujiong Xia
Chemical Communications 2017 - vol. 53(Issue 6) pp:NaN1044-1044
Publication Date(Web):2016/12/12
DOI:10.1039/C6CC08975E
The protocol presented here is a new strategy for visible light induced C–H trifluoromethylation at C4 of benzimidazoles using Togni's reagent in the presence of fac-Ir(ppy)3. Its advantages are its operational simplicity, mild reaction conditions, low catalyst loading and wide substrate scope in which electron-withdrawing, electron-donating groups and different protecting groups are tolerated.
![ACETAMIDE, N-[2-[(ACETYLOXY)METHYL]-4-CHLOROPHENYL]-](http://img.cochemist.com/ccimg/825700/825619-15-6.png)
![ACETAMIDE, N-[2-[(ACETYLOXY)METHYL]-4-CHLOROPHENYL]-](http://img.cochemist.com/ccimg/825700/825619-15-6_b.png)
![tert-Butyl 1H-benzo[d]imidazole-1-carboxylate](http://img.cochemist.com/ccimg/127200/127119-07-7.png)
![tert-Butyl 1H-benzo[d]imidazole-1-carboxylate](http://img.cochemist.com/ccimg/127200/127119-07-7_b.png)
![Acetamide, N-[2-[(acetyloxy)phenylmethyl]phenyl]-](http://img.cochemist.com/ccimg/30700/30651-46-8.png)
![Acetamide, N-[2-[(acetyloxy)phenylmethyl]phenyl]-](http://img.cochemist.com/ccimg/30700/30651-46-8_b.png)
![1,2-Dibenzyl-1H-benzo[d]imidazole](http://img.cochemist.com/ccimg/22500/22492-49-5.png)
![1,2-Dibenzyl-1H-benzo[d]imidazole](http://img.cochemist.com/ccimg/22500/22492-49-5_b.png)
![1-Benzyl-5,6-dimethyl-1H-benzo[d]imidazole](http://img.cochemist.com/ccimg/15800/15776-99-5.png)
![1-Benzyl-5,6-dimethyl-1H-benzo[d]imidazole](http://img.cochemist.com/ccimg/15800/15776-99-5_b.png)
![1H-Benzimidazole, 1-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/15800/15728-44-6.png)
![1H-Benzimidazole, 1-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/15800/15728-44-6_b.png)
![N-{2-[(4-FLUOROBENZYL)AMINO]-2-OXOETHYL}-N-(2-METHOXYBENZYL)-1,2,3-THIADIAZOLE-4-CARBOXAMIDE](http://img.cochemist.com/ccimg/5000/4981-92-4.png)
![N-{2-[(4-FLUOROBENZYL)AMINO]-2-OXOETHYL}-N-(2-METHOXYBENZYL)-1,2,3-THIADIAZOLE-4-CARBOXAMIDE](http://img.cochemist.com/ccimg/5000/4981-92-4_b.png)
![2-Chloro-1H-benzo[d]imidazole](http://img.cochemist.com/ccimg/4900/4857-06-1.png)
![2-Chloro-1H-benzo[d]imidazole](http://img.cochemist.com/ccimg/4900/4857-06-1_b.png)
![[2-(BENZYLAMINO)PHENYL]METHANOL](http://img.cochemist.com/ccimg/1800/1722-07-2.png)
![[2-(BENZYLAMINO)PHENYL]METHANOL](http://img.cochemist.com/ccimg/1800/1722-07-2_b.png)
![N-[2-(CYCLOPENTYLAMINO)-2-OXOETHYL]-N-(4-FLUOROBENZYL)-1,2,3-THIA<WBR />DIAZOLE-4-CARBOXAMIDE](http://img.cochemist.com/ccimg/800/739-88-8.png)
![N-[2-(CYCLOPENTYLAMINO)-2-OXOETHYL]-N-(4-FLUOROBENZYL)-1,2,3-THIA<WBR />DIAZOLE-4-CARBOXAMIDE](http://img.cochemist.com/ccimg/800/739-88-8_b.png)
![2,7-Bis(trifluoromethyl)-1H-benzo[d]imidazole](http://img.cochemist.com/ccimg/400/392-36-9.png)
![2,7-Bis(trifluoromethyl)-1H-benzo[d]imidazole](http://img.cochemist.com/ccimg/400/392-36-9_b.png)
![11H-PYRIDO[2,3-A]CARBAZOLE HYDROCHLORIDE (1:1)](http://img.cochemist.com/ccimg/400/384-46-3.png)
![11H-PYRIDO[2,3-A]CARBAZOLE HYDROCHLORIDE (1:1)](http://img.cochemist.com/ccimg/400/384-46-3_b.png)
![2-Propenamide, N-butyl-N-[(4-fluorophenyl)sulfonyl]-2-methyl-](/data/chemimg/3767500/1197341-60-8.png)
![2-Propenamide, N-butyl-N-[(4-fluorophenyl)sulfonyl]-2-methyl-](/data/chemimg/3767500/1197341-60-8_b.png)
![[1,1'-biphenyl]-2-carboxaldehyde, 4-methoxy-](http://img.cochemist.com/ccimg/934700/934691-48-2.png)
![[1,1'-biphenyl]-2-carboxaldehyde, 4-methoxy-](http://img.cochemist.com/ccimg/934700/934691-48-2_b.png)
![2-Propen-1-one, 1-[4-(1,1-dimethylethyl)phenyl]-3-(4-methoxyphenyl)-](http://img.cochemist.com/ccimg/914400/914335-21-0.png)
![2-Propen-1-one, 1-[4-(1,1-dimethylethyl)phenyl]-3-(4-methoxyphenyl)-](http://img.cochemist.com/ccimg/914400/914335-21-0_b.png)
![Benzenesulfonamide, N-[(1R)-2-cyano-1-phenylethyl]-4-methyl-](http://img.cochemist.com/ccimg/875600/875535-33-4.png)
![Benzenesulfonamide, N-[(1R)-2-cyano-1-phenylethyl]-4-methyl-](http://img.cochemist.com/ccimg/875600/875535-33-4_b.png)
![Benzoic acid, 4-(7-hydroxytricyclo[3.2.0.02,6]hept-7-yl)-, methyl ester](http://img.cochemist.com/ccimg/866700/866613-12-9.png)
![Benzoic acid, 4-(7-hydroxytricyclo[3.2.0.02,6]hept-7-yl)-, methyl ester](http://img.cochemist.com/ccimg/866700/866613-12-9_b.png)
![Piperidine, 1-[1-(1-naphthalenyl)-3-phenyl-2-propynyl]-](http://img.cochemist.com/ccimg/850500/850448-33-8.png)
![Piperidine, 1-[1-(1-naphthalenyl)-3-phenyl-2-propynyl]-](http://img.cochemist.com/ccimg/850500/850448-33-8_b.png)
![Aziridine, 2-[4-(1,1-dimethylethyl)phenyl]-1-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/727400/727379-98-8.png)
![Aziridine, 2-[4-(1,1-dimethylethyl)phenyl]-1-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/727400/727379-98-8_b.png)
![Benzenesulfonamide, N-[1-(azidomethyl)-2-phenylethyl]-4-methyl-](http://img.cochemist.com/ccimg/603200/603129-54-0.png)
![Benzenesulfonamide, N-[1-(azidomethyl)-2-phenylethyl]-4-methyl-](http://img.cochemist.com/ccimg/603200/603129-54-0_b.png)
![PIPERIDINE, 1-[1-(4-METHOXYPHENYL)-3-PHENYL-2-PROPYNYL]-](http://img.cochemist.com/ccimg/592600/592521-41-0.png)
![PIPERIDINE, 1-[1-(4-METHOXYPHENYL)-3-PHENYL-2-PROPYNYL]-](http://img.cochemist.com/ccimg/592600/592521-41-0_b.png)
![Piperidine, 1-[1-(4-methylphenyl)-3-phenyl-2-propynyl]-](http://img.cochemist.com/ccimg/592600/592521-36-3.png)
![Piperidine, 1-[1-(4-methylphenyl)-3-phenyl-2-propynyl]-](http://img.cochemist.com/ccimg/592600/592521-36-3_b.png)
![AZIRIDINE, 1-[(4-METHYLPHENYL)SULFONYL]-2-[(1S)-1-METHYLPROPYL]-, (2S)-](http://img.cochemist.com/ccimg/579500/579489-43-3.png)
![AZIRIDINE, 1-[(4-METHYLPHENYL)SULFONYL]-2-[(1S)-1-METHYLPROPYL]-, (2S)-](http://img.cochemist.com/ccimg/579500/579489-43-3_b.png)
![METHYL BICYCLO[2.1.1]HEXANE-5-CARBOXYLATE](http://img.cochemist.com/ccimg/565200/565184-50-1.png)
![METHYL BICYCLO[2.1.1]HEXANE-5-CARBOXYLATE](http://img.cochemist.com/ccimg/565200/565184-50-1_b.png)
![2-Propenoyl chloride, 2-[(acetyloxy)methyl]-](http://img.cochemist.com/ccimg/500800/500769-96-0.png)
![2-Propenoyl chloride, 2-[(acetyloxy)methyl]-](http://img.cochemist.com/ccimg/500800/500769-96-0_b.png)
![Benzenesulfonamide, N-[2-azido-2-(4-methoxyphenyl)ethyl]-4-methyl-](http://img.cochemist.com/ccimg/500800/500726-30-7.png)
![Benzenesulfonamide, N-[2-azido-2-(4-methoxyphenyl)ethyl]-4-methyl-](http://img.cochemist.com/ccimg/500800/500726-30-7_b.png)
![Benzenesulfonamide,N-[2-methoxy-2-(4-methoxyphenyl)ethyl]-4-methyl-](http://img.cochemist.com/ccimg/500800/500726-29-4.png)
![Benzenesulfonamide,N-[2-methoxy-2-(4-methoxyphenyl)ethyl]-4-methyl-](http://img.cochemist.com/ccimg/500800/500726-29-4_b.png)
![MORPHOLINE, 4-[1-(4-METHYLPHENYL)-3-PHENYL-2-PROPYNYL]-](http://img.cochemist.com/ccimg/433300/433232-27-0.png)
![MORPHOLINE, 4-[1-(4-METHYLPHENYL)-3-PHENYL-2-PROPYNYL]-](http://img.cochemist.com/ccimg/433300/433232-27-0_b.png)
![Aziridine, 1-[(4-methylphenyl)sulfonyl]-2-[4-(trifluoromethyl)phenyl]-](http://img.cochemist.com/ccimg/250300/250260-27-6.png)
![Aziridine, 1-[(4-methylphenyl)sulfonyl]-2-[4-(trifluoromethyl)phenyl]-](http://img.cochemist.com/ccimg/250300/250260-27-6_b.png)
![Benzaldehyde, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-](http://img.cochemist.com/ccimg/175200/175158-50-6.png)
![Benzaldehyde, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-](http://img.cochemist.com/ccimg/175200/175158-50-6_b.png)
![Benzenesulfonamide, N-[1-(azidomethyl)pentyl]-4-methyl-](http://img.cochemist.com/ccimg/175100/175086-40-5.png)
![Benzenesulfonamide, N-[1-(azidomethyl)pentyl]-4-methyl-](http://img.cochemist.com/ccimg/175100/175086-40-5_b.png)
![Aziridine, 1-[(4-methylphenyl)sulfonyl]-2-(4-nitrophenyl)-](http://img.cochemist.com/ccimg/155800/155721-37-2.png)
![Aziridine, 1-[(4-methylphenyl)sulfonyl]-2-(4-nitrophenyl)-](http://img.cochemist.com/ccimg/155800/155721-37-2_b.png)
![Aziridine, 2-(4-methoxyphenyl)-1-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/155800/155721-36-1.png)
![Aziridine, 2-(4-methoxyphenyl)-1-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/155800/155721-36-1_b.png)
![4'-Chloro-[1,1'-biphenyl]-2-carbaldehyde](http://img.cochemist.com/ccimg/153900/153850-83-0.png)
![4'-Chloro-[1,1'-biphenyl]-2-carbaldehyde](http://img.cochemist.com/ccimg/153900/153850-83-0_b.png)
![Benzenemethanol, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-](http://img.cochemist.com/ccimg/149200/149170-33-2.png)
![Benzenemethanol, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-](http://img.cochemist.com/ccimg/149200/149170-33-2_b.png)
![Aziridine, 1-[(4-methylphenyl)sulfonyl]-2,3-diphenyl-](http://img.cochemist.com/ccimg/147100/147054-74-8.png)
![Aziridine, 1-[(4-methylphenyl)sulfonyl]-2,3-diphenyl-](http://img.cochemist.com/ccimg/147100/147054-74-8_b.png)
![Aziridine, 2-methyl-1-[(4-methylphenyl)sulfonyl]-3-phenyl-, trans-](http://img.cochemist.com/ccimg/137600/137595-21-2.png)
![Aziridine, 2-methyl-1-[(4-methylphenyl)sulfonyl]-3-phenyl-, trans-](http://img.cochemist.com/ccimg/137600/137595-21-2_b.png)
![Aziridine, 1-[(4-methylphenyl)sulfonyl]-2-(2-methylpropyl)-, (S)-](http://img.cochemist.com/ccimg/124600/124575-31-1.png)
![Aziridine, 1-[(4-methylphenyl)sulfonyl]-2-(2-methylpropyl)-, (S)-](http://img.cochemist.com/ccimg/124600/124575-31-1_b.png)
![Benzene, 1,2,3-trimethoxy-5-[(phenylthio)methyl]-](http://img.cochemist.com/ccimg/123800/123731-52-2.png)
![Benzene, 1,2,3-trimethoxy-5-[(phenylthio)methyl]-](http://img.cochemist.com/ccimg/123800/123731-52-2_b.png)
![1,3-Benzodioxole, 5-[(phenylthio)methyl]-](http://img.cochemist.com/ccimg/103900/103844-15-1.png)
![1,3-Benzodioxole, 5-[(phenylthio)methyl]-](http://img.cochemist.com/ccimg/103900/103844-15-1_b.png)
![2-Propenal, 3-[1,1'-biphenyl]-2-yl-](http://img.cochemist.com/ccimg/100500/100430-86-2.png)
![2-Propenal, 3-[1,1'-biphenyl]-2-yl-](http://img.cochemist.com/ccimg/100500/100430-86-2_b.png)
![Aziridine, 2-(4-chlorophenyl)-1-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/97500/97401-93-9.png)
![Aziridine, 2-(4-chlorophenyl)-1-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/97500/97401-93-9_b.png)
![Aziridine, 2-(4-methylphenyl)-1-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/97500/97401-87-1.png)
![Aziridine, 2-(4-methylphenyl)-1-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/97500/97401-87-1_b.png)
![Phosphonium, [(3-fluorophenyl)methyl]triphenyl-, bromide](http://img.cochemist.com/ccimg/89400/89302-81-8.png)
![Phosphonium, [(3-fluorophenyl)methyl]triphenyl-, bromide](http://img.cochemist.com/ccimg/89400/89302-81-8_b.png)
![Benzene, 1,2-dimethoxy-4-[(phenylthio)methyl]-](http://img.cochemist.com/ccimg/83400/83318-94-9.png)
![Benzene, 1,2-dimethoxy-4-[(phenylthio)methyl]-](http://img.cochemist.com/ccimg/83400/83318-94-9_b.png)
![NAPHTHO[1,2-B]FURAN, 2-(4-METHOXYPHENYL)-](http://img.cochemist.com/ccimg/80600/80554-45-6.png)
![NAPHTHO[1,2-B]FURAN, 2-(4-METHOXYPHENYL)-](http://img.cochemist.com/ccimg/80600/80554-45-6_b.png)
![Methanone, (3-methoxyphenyl)[2-(4-methoxyphenyl)cyclopropyl]-](http://img.cochemist.com/ccimg/75000/74973-33-4.png)
![Methanone, (3-methoxyphenyl)[2-(4-methoxyphenyl)cyclopropyl]-](http://img.cochemist.com/ccimg/75000/74973-33-4_b.png)
![1,4-Butanedione, 4-[4-(1,1-dimethylethyl)phenyl]-1,2-diphenyl-](http://img.cochemist.com/ccimg/65700/65691-18-1.png)
![1,4-Butanedione, 4-[4-(1,1-dimethylethyl)phenyl]-1,2-diphenyl-](http://img.cochemist.com/ccimg/65700/65691-18-1_b.png)
![Phosphonium, [(2-methoxyphenyl)methyl]triphenyl-, bromide](http://img.cochemist.com/ccimg/64900/64820-07-1.png)
![Phosphonium, [(2-methoxyphenyl)methyl]triphenyl-, bromide](http://img.cochemist.com/ccimg/64900/64820-07-1_b.png)
![Phosphonium, [(2-chlorophenyl)methyl]triphenyl-, bromide](http://img.cochemist.com/ccimg/62700/62640-67-9.png)
![Phosphonium, [(2-chlorophenyl)methyl]triphenyl-, bromide](http://img.cochemist.com/ccimg/62700/62640-67-9_b.png)
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![2-Propen-1-one, 1-[4-(1,1-dimethylethyl)phenyl]-](http://img.cochemist.com/ccimg/46300/46249-51-8_b.png)
![3'-Methoxy-[1,1'-biphenyl]-2-carboxaldehyde](http://img.cochemist.com/ccimg/38500/38491-36-0.png)
![3'-Methoxy-[1,1'-biphenyl]-2-carboxaldehyde](http://img.cochemist.com/ccimg/38500/38491-36-0_b.png)
![{[4-(BENZYLOXY)PHENYL]ETHYNYL}(TRIMETHYL)SILANE](http://img.cochemist.com/ccimg/36200/36132-95-3.png)
![{[4-(BENZYLOXY)PHENYL]ETHYNYL}(TRIMETHYL)SILANE](http://img.cochemist.com/ccimg/36200/36132-95-3_b.png)
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![METHANONE, PHENYLTRICYCLO[3.3.1.1(3,7)]DEC-1-YL-](http://img.cochemist.com/ccimg/32000/31919-47-8_b.png)
![METHYL 1-AZABICYCLO[2.2.2]OCT-2-ENE-3-CARBOXYLATE](http://img.cochemist.com/ccimg/30500/30418-53-2.png)
![METHYL 1-AZABICYCLO[2.2.2]OCT-2-ENE-3-CARBOXYLATE](http://img.cochemist.com/ccimg/30500/30418-53-2_b.png)
![4'-Methyl-[1,1'-biphenyl]-2-carbaldehyde](http://img.cochemist.com/ccimg/16200/16191-28-9.png)
![4'-Methyl-[1,1'-biphenyl]-2-carbaldehyde](http://img.cochemist.com/ccimg/16200/16191-28-9_b.png)
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![[1,1'-Biphenyl]-2-carboxaldehyde,4'-methoxy-](http://img.cochemist.com/ccimg/16100/16064-04-3_b.png)
![Benzene,1-methoxy-4-[(phenylthio)methyl]-](http://img.cochemist.com/ccimg/5100/5023-67-6.png)
![Benzene,1-methoxy-4-[(phenylthio)methyl]-](http://img.cochemist.com/ccimg/5100/5023-67-6_b.png)
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![Benzene, 1-methyl-4-[(phenylthio)methyl]-](http://img.cochemist.com/ccimg/5100/5023-65-4_b.png)
![5-(Bromomethyl)benzo[d][1,3]dioxole](http://img.cochemist.com/ccimg/2700/2606-51-1.png)
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![Phosphonium,[(3-methylphenyl)methyl]triphenyl-, bromide (1:1)](http://img.cochemist.com/ccimg/1800/1702-41-6_b.png)
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![Aziridine, 1-[(4-methylphenyl)sulfonyl]-2-phenyl-, (2S)-](http://img.cochemist.com/ccimg/149800/149769-84-6_b.png)
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![Aziridine, 2-butyl-1-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/117000/116905-61-4_b.png)
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![Aziridine,1-[(4-methylphenyl)sulfonyl]-2-phenyl-](http://img.cochemist.com/ccimg/24400/24395-14-0_b.png)
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![Indeno[1,2-b]azirine, 1,1a,6,6a-tetrahydro-1-[(4-methylphenyl)sulfonyl]-](/data/chemimg/3768100/17798-14-0_b.png)
![Benzenemethanol, 4-(1,1-dimethylethyl)-α-[4-(1,1-dimethylethyl)phenyl]-](/data/chemimg/1137300/16607-60-6.png)
![Benzenemethanol, 4-(1,1-dimethylethyl)-α-[4-(1,1-dimethylethyl)phenyl]-](/data/chemimg/1137300/16607-60-6_b.png)
