Zheng-Hui Guan

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Name: 关正辉
Organization: Northwest University , China
Department: Department of Chemistry & Materials Science
Title: NULL(PhD)
Co-reporter:Shun Wang, Yong-Qiang Guo, Zhi-Hui Ren, Yao-Yu Wang, and Zheng-Hui Guan
Organic Letters April 7, 2017 Volume 19(Issue 7) pp:
Publication Date(Web):March 14, 2017
DOI:10.1021/acs.orglett.7b00389
A novel K2CO3-mediated cyclization and rearrangement of γ,δ-alkynyl oximes for the synthesis of pyridols is described. The process accomplishes an efficient [1,3] rearrangement of the O-vinyl oxime intermediate which is in situ generated from the intramolecular nucleophilic addition of γ,δ-alkynyl oximes. The reaction employs readily accessible starting materials, tolerates a wide range of functional groups, and gives a variety of synthetically challenging pyridols in good yields.
Co-reporter:Ming Chen;Le Yu;Zhi-Hui Ren;Yao-Yu Wang
Chemical Communications 2017 vol. 53(Issue 46) pp:6243-6246
Publication Date(Web):2017/06/06
DOI:10.1039/C7CC02852K
A novel palladium-catalyzed regioselective oxidative carbonylation of tri-substituted alkenes with CO and alcohols for the synthesis of α,β-unsaturated esters has been developed. Experimental studies and DFT calculations suggested that the reaction proceeded through alkoxylation of the palladium(II) catalyst, CO and CC double bond migratory insertion, β-(N)H elimination and tautomerization cascade steps. The reaction tolerates a wide range of groups and produces valuable aminomethylenemalonates in high yields.
Co-reporter:YuKun Yi;Mi-Na Zhao;Zhi-Hui Ren;Yao-Yu Wang
Green Chemistry (1999-Present) 2017 vol. 19(Issue 4) pp:1023-1027
Publication Date(Web):2017/02/21
DOI:10.1039/C6GC03137D
A novel and facile iron-catalyzed cyclization of ketoxime acetates and aldehydes for the green synthesis of substituted pyridines has been developed. In the presence of a FeCl3 catalyst, this reaction exhibited a good functional group tolerance to produce 2,4,6-triarylsubstituted symmetrical pyridines in high yields in the absence of any additive. A gram-scale reaction sequence was performed to demonstrate the scaled-up applicability of this synthetic method.
Co-reporter:Muhammad Usman;Zhi-Hui Ren;Yao-Yu Wang
Organic & Biomolecular Chemistry 2017 vol. 15(Issue 5) pp:1091-1095
Publication Date(Web):2017/02/01
DOI:10.1039/C6OB02627C
A new Cu-catalyzed efficient protocol is described for the transformation of oximes to the corresponding carbonate derivatives. Diisopropyl azodicarboxylate acted as a selective new precursor for the synthesis of oxime carbonates in high yields. The O–H bond cleavage and O–C bond formation occur in the presence of a copper catalyst providing a synthetically useful process, which tolerates a wide range of functional groups.
Co-reporter:Mi-Na Zhao;Le Yu;Nan-Fang Mo;Zhi-Hui Ren;Yao-Yu Wang
Organic Chemistry Frontiers 2017 vol. 4(Issue 4) pp:597-602
Publication Date(Web):2017/03/28
DOI:10.1039/C6QO00809G
An efficient iron-catalyzed cyclization of ketoxime acetates with N,N-dimethylaniline for the synthesis of symmetrical pyridines has been developed. A methyl carbon on N,N-dimethylaniline acts as a source of one carbon synthons. The reaction used readily available starting materials, tolerated various functional groups, and afforded 2,3,5,6-tetrasubstituted symmetrical pyridines in good yields.
Co-reporter:Mi-Na Zhao, Le Yu, Rong-Rong Hui, Zhi-Hui Ren, Yao-Yu Wang, and Zheng-Hui Guan
ACS Catalysis 2016 Volume 6(Issue 6) pp:3473
Publication Date(Web):April 28, 2016
DOI:10.1021/acscatal.6b00849
An iron-catalyzed dehydrogenative [4 + 2] cycloaddition reaction of tertiary anilines and enamides for the synthesis of tetrahydroquinolines with amido-substituted quaternary carbon centers has been developed. The reaction proceeds through iron-catalyzed dehydrogenation of tertiary anilines followed by nucleophilic addition/intramolecular cyclization with enamides to afford tetrahydroquinolines with amido-substituted quaternary carbon centers in good yields. The reaction tolerates a wide range of functional groups and proceeds under mild conditions. The mechanism for the dehydrogenative [4 + 2] cycloaddition has been confirmed by DFT calculations.Keywords: dehydrogenative [4 + 2] cycloaddition; enamide; iron-catalyzed; tertiary anilines; tetrahydroquinoline
Co-reporter:Mi-Na Zhao, Zhi-Hui Ren, Le Yu, Yao-Yu Wang, and Zheng-Hui Guan
Organic Letters 2016 Volume 18(Issue 5) pp:1194-1197
Publication Date(Web):February 24, 2016
DOI:10.1021/acs.orglett.6b00326
A novel and efficient iron-catalyzed cyclization of ketoxime carboxylates and N,N-dialkylanilines for the modular synthesis of diverse pyridines was developed. The reaction was initiated by Fe-catalyzed N–O bond cleavage of ketoxime carboxylates in the presence of tertiary anilines. The methylene carbon on N,N-dialkylanilines functioned as a source of one-carbon synthon in the reaction. The reaction used readily available starting materials, tolerated various functional groups, and afforded 2,4-disubstituted and 2,4,6-trisubstituted pyridines in good to high yields under mild conditions.
Co-reporter:Peng Gao, Juan Wang, Zi-Jing Bai, Li Shen, Yun-Yun Yan, De-Suo Yang, Ming-Jin Fan, and Zheng-Hui Guan
Organic Letters 2016 Volume 18(Issue 23) pp:6074-6077
Publication Date(Web):November 15, 2016
DOI:10.1021/acs.orglett.6b03060
A novel K2S2O8-promoted oxidative cyclization of enamines is described. A variety of enamines having diverse functional groups and substitution patterns react well using K2S2O8 as the oxidant in the absence of catalyst. This protocol provides a very simple route for the synthesis of polycarbonyl pyrroles and has the advantages of readily available starting materials, mild reaction conditions, and a wide scope of substrates.
Co-reporter:Mei-Na Zhang, Mi-Na Zhao, Ming Chen, Zhi-Hui Ren, Yao-Yu Wang and Zheng-Hui Guan  
Chemical Communications 2016 vol. 52(Issue 36) pp:6127-6130
Publication Date(Web):05 Apr 2016
DOI:10.1039/C6CC01942K
A novel and efficient copper-catalyzed radical cross-coupling of 1,3-dicarbonyl compounds with terminal alkenes for the synthesis of tetracarbonyl compounds with a quaternary carbon atom has been developed. Mechanistically, this transformation involves the construction of two C–C bonds and two CO bonds in a one-pot process. The reaction tolerates a wide range of functional groups and proceeds under mild conditions.
Co-reporter:Ni-Ni Zhou, Hai-Tao Zhu, De-Suo Yang and Zheng-Hui Guan  
Organic & Biomolecular Chemistry 2016 vol. 14(Issue 30) pp:7136-7149
Publication Date(Web):14 Jun 2016
DOI:10.1039/C6OB00962J
Pyrroles are important synthetic targets as a result of their occurrence in numerous biologically active molecules, their important roles in diverse living processes, and their utility as versatile intermediates. As a consequence, numerous efforts focused on the development of concise and efficient methods for the construction of pyrroles. Compared with other transition metals, the group 1B metals (Cu, Ag and Au) are probably more versatile and widely used for the synthesis of pyrroles in organic chemistry. Considering the importance of both topics in organic synthesis, here we summarize recent achievements in the synthesis of pyrroles catalyzed by monometallic systems which belong to the group 1B metals (Cu, Ag and Au).
Co-reporter:Zhi-Hui Ren, Mi-Na Zhao and Zheng-Hui Guan  
RSC Advances 2016 vol. 6(Issue 20) pp:16516-16519
Publication Date(Web):05 Feb 2016
DOI:10.1039/C5RA27899F
An efficient copper(I)-catalyzed oxidative tetrahydrofuranylation of oximes has been developed. This reaction shows good functional group tolerance and various substituted ketoximes and aldoximes coupled smoothly with THF to give the corresponding O-tetrahydrofuran-2-yl oxime ethers in high yields.
Co-reporter:Shun-Jiang Yao, Zhi-Hui Ren, Zheng-Hui Guan
Tetrahedron Letters 2016 Volume 57(Issue 35) pp:3892-3901
Publication Date(Web):31 August 2016
DOI:10.1016/j.tetlet.2016.07.063
•Acylation of indoles.•Introduced the diverse carbonyl sources.•Intramolecular cyclization of aminoalkynes and enaminones.Acylindoles are valuable chemicals widely found in natural products, pharmaceuticals, and biologically active compounds. They are also important synthetic building blocks for chemical transformation. Recent advances of acylindoles synthesis via acylation of indoles with diverse carbonyl sources (N-alkylamines, aldehydes, α-oxocarboxylic acids, nitriles, olefins, CO, fluorinated acetic acids (salts), and diketones) are highly desirable methods. Moreover, intramolecular cyclization of aminoalkynes and enaminones also provided highly efficient and atom-economical alternatives to the traditional methods. Herein, we summarize recent advances on the synthesis of acylindoles.Figure optionsDownload full-size imageDownload as PowerPoint slide
Co-reporter:Shun-Jiang Yao, Zhi-Hui Ren, Yao-Yu Wang, and Zheng-Hui Guan
The Journal of Organic Chemistry 2016 Volume 81(Issue 10) pp:4226-4234
Publication Date(Web):April 21, 2016
DOI:10.1021/acs.joc.6b00580
A simple and efficient protocol for the fluoroacetylation of indoles is reported. The reaction uses fluorinated acetic acids as the fluoroacetylation reagents to synthesize diverse fluoromethyl indol-3-yl ketones in good yields under catalyst- and additive-free conditions. In addition, the only byproduct is water in this transformation. The synthetic utility of this reaction was also demonstrated by the concise synthesis of α-(trifluoromethyl)(indol-3-yl)methanol and indole-3-carboxylic acid.
Co-reporter:Mi-Na Zhao, Longfei Ran, Ming Chen, Zhi-Hui Ren, Yao-Yu Wang, and Zheng-Hui Guan
ACS Catalysis 2015 Volume 5(Issue 2) pp:1210
Publication Date(Web):January 20, 2015
DOI:10.1021/cs5019106
A novel palladium-catalyzed carbonylation of indoles with CO and aromatic boronic acids for the synthesis of indol-3-yl aryl ketones was developed. The reaction tolerates a wide range of functional groups and gives a variety of valuable indol-3-yl aryl ketones in high yields under mild conditions.Keywords: arylboronic acids; carbonylation; indol-3-yl aryl ketones; indoles; palladium-catalyzed
Co-reporter:Ming Chen, Zhi-Hui Ren, Yao-Yu Wang, and Zheng-Hui Guan
The Journal of Organic Chemistry 2015 Volume 80(Issue 2) pp:1258-1263
Publication Date(Web):December 19, 2014
DOI:10.1021/jo502581p
A Pd(II)-catalyzed C–H monocarbonylation of N-alkylanilines for the synthesis of o-aminobenzoates has been developed. Various aliphatic alcohols and phenol were tolerated in the reaction to afford the corresponding o-aminobenzoates in good yields under mild balloon pressure of CO.
Co-reporter:Longfei Ran, Zhi-Hui Ren, Yao-Yu Wang and Zheng-Hui Guan  
Green Chemistry 2014 vol. 16(Issue 1) pp:112-115
Publication Date(Web):14 Oct 2013
DOI:10.1039/C3GC41800F
A novel and efficient copper-catalyzed homocoupling of ketoxime carboxylates has been developed for the synthesis of symmetrical pyrroles. This reaction tolerates a wide range of functional groups and provides a synthetically useful process to synthesize valuable symmetrical pyrroles under mild conditions.
Co-reporter:Xue-Jing Quan, Zhi-Hui Ren, Yao-Yu Wang, and Zheng-Hui Guan
Organic Letters 2014 Volume 16(Issue 21) pp:5728-5731
Publication Date(Web):October 24, 2014
DOI:10.1021/ol5027975
A p-TsOH-mediated 1,3-dipolar cycloaddition of nitroolefins and sodium azide for the synthesis of 4-aryl-NH-1,2,3-triazoles has been developed. p-TsOH was discovered as a vital additive in this type of 1,3-dipolar cycloaddition. This novel cycloaddition reaction is a good method for the rapid synthesis of valuable 4-aryl-NH-1,2,3-triazoles in high yields.
Co-reporter:Zhi-Jing Zhang, Xue-Jing Quan, Zhi-Hui Ren, Yao-Yu Wang, and Zheng-Hui Guan
Organic Letters 2014 Volume 16(Issue 12) pp:3292-3295
Publication Date(Web):June 4, 2014
DOI:10.1021/ol501293c
A facile benzoyl peroxide (BPO) mediated ortho-hydroxylation and benzoylation of N-alkyl anilines for the synthesis of 2-benzamidophenols has been developed. The reaction tolerates a wide range of functional groups and is a good method for the straightforward synthesis of valuable 2-benzamidophenols in good yields under mild conditions.
Co-reporter:Xiao-Li Lian, Zhi-Hui Ren, Yao-Yu Wang, and Zheng-Hui Guan
Organic Letters 2014 Volume 16(Issue 12) pp:3360-3363
Publication Date(Web):June 12, 2014
DOI:10.1021/ol501394k
A novel and efficient palladium-catalyzed intramolecular oxidative cyclization of tertiary enamines for the synthesis of 1,3,4-trisubstituted pyrroles and 1,3-disubstituted indoles has been developed. Trifluoroacetic acid plays an important role in the reaction. A series of pyrroles and indoles with substitution patterns that are not easily accessible by traditional routes were synthesized in good yields under mild conditions.
Co-reporter:Mi-Na Zhao, Rong-Rong Hui, Zhi-Hui Ren, Yao-Yu Wang, and Zheng-Hui Guan
Organic Letters 2014 Volume 16(Issue 11) pp:3082-3085
Publication Date(Web):May 13, 2014
DOI:10.1021/ol501183z
A novel ruthenium-catalyzed cyclization of ketoxime carboxylates with N,N-dimethylformamide (DMF) for the synthesis of tetrasubstituted symmetrical pyridines has been developed. A methyl carbon on DMF performed as a source of a one carbon synthon. And NaHSO3 plays a role in the reaction.
Co-reporter:Mi-Na Zhao, Zhi-Hui Ren, Yao-Yu Wang, and Zheng-Hui Guan
Organic Letters 2014 Volume 16(Issue 2) pp:608-611
Publication Date(Web):January 9, 2014
DOI:10.1021/ol403517p
A novel and efficient palladium(II)-catalyzed alkenyl C–H activation oxidative annulation of enamides with alkynes for the synthesis of substituted pyrroles has been developed. The reaction tolerates a wide range of functional groups and is a reliable method for the synthesis of triaryl-substituted pyrroles in high yields.
Co-reporter:Wei Du, Mi-Na Zhao, Zhi-Hui Ren, Yao-Yu Wang and Zheng-Hui Guan  
Chemical Communications 2014 vol. 50(Issue 56) pp:7437-7439
Publication Date(Web):19 May 2014
DOI:10.1039/C4CC03129F
A novel and facile copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates for the synthesis of 2-arylpyrroles has been developed. The reaction tolerates a range of functional groups and is a practical procedure for rapid synthesis of 2-arylpyrroles in high yields under mild conditions.
Co-reporter:Mi-Na Zhao, Xiao-Li Lian, Zhi-Hui Ren, Yao-Yu Wang and Zheng-Hui Guan  
RSC Advances 2014 vol. 4(Issue 107) pp:62042-62045
Publication Date(Web):12 Nov 2014
DOI:10.1039/C4RA11543K
An efficient palladium-catalyzed oxidative amination of olefins with secondary anilines for the synthesis of tertiary (E)-enamines has been developed. Trimethylacetic acid (PivOH) played an important role in the reaction. This protocol tolerates a range of functional groups and is a reliable method for direct synthesis of tertiary (E)-enamines in high yields under mild conditions.
Co-reporter:Mi-Na Zhao;Zhi-Hui Ren; Yao-Yu Wang ;Dr. Zheng-Hui Guan
Chemistry - A European Journal 2014 Volume 20( Issue 7) pp:1839-1842
Publication Date(Web):
DOI:10.1002/chem.201304565

Abstract

An efficient copper-promoted oxidative coupling of enamides with alkynes has been developed for the synthesis of substituted pyrroles. The reaction proceeded through CH and NH bond functionalization of enamides under mild conditions.

Co-reporter:Longfei Ran;Zhi-Hui Ren; Yao-Yu Wang ;Dr. Zheng-Hui Guan
Chemistry – An Asian Journal 2014 Volume 9( Issue 2) pp:577-583
Publication Date(Web):
DOI:10.1002/asia.201301245

Abstract

A novel and efficient palladium-catalyzed aminocarbonylation of aryl iodides with amides and N-alkyl anilines has been developed. The reaction tolerates a wide range of functional groups and is a reliable method for the rapid synthesis of a variety of valuable imides and tertiary benzanilides under an atmospheric pressure of CO.

Co-reporter:Sha Gao, Ming Chen, Mi-Na Zhao, Wei Du, Zhi-Hui Ren, Yao-Yu Wang, and Zheng-Hui Guan
The Journal of Organic Chemistry 2014 Volume 79(Issue 9) pp:4196-4200
Publication Date(Web):April 10, 2014
DOI:10.1021/jo500417u
A novel palladium-catalyzed oxidative double carbonylation of o-iodoanilines for the synthesis of isatoic anhydrides has been developed. The reaction employs readily available o-iodoanilines as the starting materials and proceeds under mild conditions. For extension, palladium-catalyzed oxidative carbonylation of anthranilic acids was developed for the synthesis of substituted isatoic anhydrides in high to excellent yields.
Co-reporter:Xiao-Li Lian, Hao Lei, Xue-Jing Quan, Zhi-Hui Ren, Yao-Yu Wang and Zheng-Hui Guan  
Chemical Communications 2013 vol. 49(Issue 74) pp:8196-8198
Publication Date(Web):17 Jul 2013
DOI:10.1039/C3CC44215B
A novel and efficient method for the oxidation of 2-arylindoles to synthesize 2-arylbenzoxazinones utilizing oxone as the sole oxidant has been developed. The reaction tolerates a wide range of functional groups and allows quick and atom-economical assembly of a variety of valuable 2-arylbenzoxazinones in high yields.
Co-reporter:Zhi-Jing Zhang, Zhi-Hui Ren, Yao-Yu Wang, and Zheng-Hui Guan
Organic Letters 2013 Volume 15(Issue 18) pp:4822-4825
Publication Date(Web):August 29, 2013
DOI:10.1021/ol4022222
A novel Cu(TFA)2-catalyzed oxidative tandem cyclization/1,2-alkyl migration of readily available enamino amides for the synthesis of pyrrolin-4-ones has been developed. The reaction tolerates a wide range of functional groups and is a reliable method for the rapid synthesis of substituted pyrrolin-4-ones in high yields under mild conditions.
Co-reporter:Mi-Na Zhao;Hao Liang;Zhi-Hui Ren
Advanced Synthesis & Catalysis 2013 Volume 355( Issue 1) pp:221-226
Publication Date(Web):
DOI:10.1002/adsc.201200673

Abstract

The iron-catalyzed addition and cyclization of the Blaise reaction intermediate and nitroolefins to synthesize highly functionalized NH-pyrroles in a tandem one-pot manner from nitriles has been developed. This reaction shows good functional group tolerance and affords a broad spectrum of substituted NH-pyrroles in good yields.

Co-reporter:Mi-Na Zhao;Wei Du;Zhi-Hui Ren;Yao-Yu Wang
European Journal of Organic Chemistry 2013 Volume 2013( Issue 35) pp:7989-7995
Publication Date(Web):
DOI:10.1002/ejoc.201301005

Abstract

The FeCl3-catalyzed self-condensation of enamides offers a new strategy for the synthesis of enamido-substituted nitrogen-containing quaternary carbon centers, which are attractive structures in organic chemistry. The reaction affords nitrogen-containing quaternary carbon centers in good yields under mild reaction conditions. The catalytic system was also employed in the condensation of enamides with indoles for the synthesis of bis-indoles.

Co-reporter:Hao Liang;Zhi-Hui Ren; Yao-Yu Wang ;Dr. Zheng-Hui Guan
Chemistry - A European Journal 2013 Volume 19( Issue 30) pp:9789-9794
Publication Date(Web):
DOI:10.1002/chem.201301785
Co-reporter:Ming Chen;Zhi-Hui Ren; Yao-Yu Wang ;Dr. Zheng-Hui Guan
Angewandte Chemie 2013 Volume 125( Issue 52) pp:14446-14449
Publication Date(Web):
DOI:10.1002/ange.201307942
Co-reporter:Ming Chen;Zhi-Hui Ren; Yao-Yu Wang ;Dr. Zheng-Hui Guan
Angewandte Chemie International Edition 2013 Volume 52( Issue 52) pp:14196-14199
Publication Date(Web):
DOI:10.1002/anie.201307942
Co-reporter:Zheng-Hui Guan ; Ming Chen ;Zhi-Hui Ren
Journal of the American Chemical Society 2012 Volume 134(Issue 42) pp:17490-17493
Publication Date(Web):October 10, 2012
DOI:10.1021/ja308976x
A Pd-catalyzed regioselective C–H bond carbonylation of N-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is a reliable method for the rapid elaboration of readily available N-alkyl anilines into a variety of substituted isatoic anhydrides under mild conditions.
Co-reporter:Mi-Na Zhao, Zhi-Hui Ren, Yao-Yu Wang and Zheng-Hui Guan  
Chemical Communications 2012 vol. 48(Issue 65) pp:8105-8107
Publication Date(Web):27 Jun 2012
DOI:10.1039/C2CC33768A
A novel and general procedure for Cu-catalyzed coupling of enamides with alkynes to synthesize substituted pyridines was developed. The chemistry was allowed to extend to the synthesis of substituted isoquinolines by coupling of enamides with arynes under transition-metal-free conditions.
Co-reporter:Liang Li, Mi-Na Zhao, Zhi-Hui Ren, Jian-Li Li, and Zheng-Hui Guan
Organic Letters 2012 Volume 14(Issue 13) pp:3506-3509
Publication Date(Web):June 22, 2012
DOI:10.1021/ol3014733
New strategies for the oxidative cycloaddition of enones with enamines are developed. These cycloaddition reactions directly afford substituted aromatic amines, which are important in organic chemistry, in moderate to good yield. Cu(OAc)2/TFA is shown to be essential to achieve high reaction efficiency.
Co-reporter:Zheng-Hui Guan;Hao Lei;Ming Chen;Zhi-Hui Ren;Yinjuan Bai ;Yao-Yu Wang
Advanced Synthesis & Catalysis 2012 Volume 354( Issue 2-3) pp:489-496
Publication Date(Web):
DOI:10.1002/adsc.201100545

Abstract

Switchable access to carbamates and ureas has been developed by solvent control palladium-catalyzed carbonylation of aromatic amines under an atmosphere of carbon monoxide. A variety of N-phenylcarbamates and N,N′-diphenylureas was easily synthesized in good to excellent yields from readily available aromatic amines under mild conditions.

Co-reporter:Zheng-Hui Guan, Liang Li, Zhi-Hui Ren, Jianli Li and Mi-Na Zhao  
Green Chemistry 2011 vol. 13(Issue 7) pp:1664-1668
Publication Date(Web):21 Apr 2011
DOI:10.1039/C1GC15278E
A facile and efficient method for the synthesis of substituted pyrroles from enaminoesters and nitroolefins is reported. This general procedure provides a wide variety of multisubstituted pyrroles in good to excellent yields under mild reaction conditions.
Co-reporter:Mi-Na Zhao, Mei-Na Zhang, Zhi-Hui Ren, Yao-Yu Wang, Zheng-Hui Guan
Science Bulletin (15 April 2017) Volume 62(Issue 7) pp:493-496
Publication Date(Web):15 April 2017
DOI:10.1016/j.scib.2017.03.003
A novel 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-mediated formal cycloaddition of β,γ-alkenyl esters with p-tolylsulfonylazide (p-TsN3) for the synthesis of 3,5-disubstituted pyrazoles has been developed. The reaction proceeded through diazotization of β,γ-alkenyl esters sequential with thermodynamic cyclization. p-Tolylsulfonylazide played a role as a source of two-nitrogen synthons. The reaction employs readily available starting materials, tolerates a wide range of functional groups, and proceeds under mild conditions.An efficient DBU-mediated formal [3+2] cycloaddition of β,γ-alkenyl esters with p-tolylsulfonylazide (p-TsN3) for the synthesis of 3,5-disubstituted pyrazoles has been developed.Download high-res image (73KB)Download full-size image
Co-reporter:Mei-Na Zhang, Mi-Na Zhao, Ming Chen, Zhi-Hui Ren, Yao-Yu Wang and Zheng-Hui Guan
Chemical Communications 2016 - vol. 52(Issue 36) pp:NaN6130-6130
Publication Date(Web):2016/04/05
DOI:10.1039/C6CC01942K
A novel and efficient copper-catalyzed radical cross-coupling of 1,3-dicarbonyl compounds with terminal alkenes for the synthesis of tetracarbonyl compounds with a quaternary carbon atom has been developed. Mechanistically, this transformation involves the construction of two C–C bonds and two CO bonds in a one-pot process. The reaction tolerates a wide range of functional groups and proceeds under mild conditions.
Co-reporter:Xiao-Li Lian, Hao Lei, Xue-Jing Quan, Zhi-Hui Ren, Yao-Yu Wang and Zheng-Hui Guan
Chemical Communications 2013 - vol. 49(Issue 74) pp:NaN8198-8198
Publication Date(Web):2013/07/17
DOI:10.1039/C3CC44215B
A novel and efficient method for the oxidation of 2-arylindoles to synthesize 2-arylbenzoxazinones utilizing oxone as the sole oxidant has been developed. The reaction tolerates a wide range of functional groups and allows quick and atom-economical assembly of a variety of valuable 2-arylbenzoxazinones in high yields.
Co-reporter:Wei Du, Mi-Na Zhao, Zhi-Hui Ren, Yao-Yu Wang and Zheng-Hui Guan
Chemical Communications 2014 - vol. 50(Issue 56) pp:NaN7439-7439
Publication Date(Web):2014/05/19
DOI:10.1039/C4CC03129F
A novel and facile copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates for the synthesis of 2-arylpyrroles has been developed. The reaction tolerates a range of functional groups and is a practical procedure for rapid synthesis of 2-arylpyrroles in high yields under mild conditions.
Co-reporter:Mi-Na Zhao, Zhi-Hui Ren, Yao-Yu Wang and Zheng-Hui Guan
Chemical Communications 2012 - vol. 48(Issue 65) pp:NaN8107-8107
Publication Date(Web):2012/06/27
DOI:10.1039/C2CC33768A
A novel and general procedure for Cu-catalyzed coupling of enamides with alkynes to synthesize substituted pyridines was developed. The chemistry was allowed to extend to the synthesis of substituted isoquinolines by coupling of enamides with arynes under transition-metal-free conditions.
Co-reporter:Ni-Ni Zhou, Hai-Tao Zhu, De-Suo Yang and Zheng-Hui Guan
Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 30) pp:NaN7149-7149
Publication Date(Web):2016/06/14
DOI:10.1039/C6OB00962J
Pyrroles are important synthetic targets as a result of their occurrence in numerous biologically active molecules, their important roles in diverse living processes, and their utility as versatile intermediates. As a consequence, numerous efforts focused on the development of concise and efficient methods for the construction of pyrroles. Compared with other transition metals, the group 1B metals (Cu, Ag and Au) are probably more versatile and widely used for the synthesis of pyrroles in organic chemistry. Considering the importance of both topics in organic synthesis, here we summarize recent achievements in the synthesis of pyrroles catalyzed by monometallic systems which belong to the group 1B metals (Cu, Ag and Au).
Co-reporter:Muhammad Usman, Zhi-Hui Ren, Yao-Yu Wang and Zheng-Hui Guan
Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 5) pp:NaN1095-1095
Publication Date(Web):2017/01/04
DOI:10.1039/C6OB02627C
A new Cu-catalyzed efficient protocol is described for the transformation of oximes to the corresponding carbonate derivatives. Diisopropyl azodicarboxylate acted as a selective new precursor for the synthesis of oxime carbonates in high yields. The O–H bond cleavage and O–C bond formation occur in the presence of a copper catalyst providing a synthetically useful process, which tolerates a wide range of functional groups.
Co-reporter:Ming Chen, Le Yu, Zhi-Hui Ren, Yao-Yu Wang and Zheng-Hui Guan
Chemical Communications 2017 - vol. 53(Issue 46) pp:NaN6246-6246
Publication Date(Web):2017/05/10
DOI:10.1039/C7CC02852K
A novel palladium-catalyzed regioselective oxidative carbonylation of tri-substituted alkenes with CO and alcohols for the synthesis of α,β-unsaturated esters has been developed. Experimental studies and DFT calculations suggested that the reaction proceeded through alkoxylation of the palladium(II) catalyst, CO and CC double bond migratory insertion, β-(N)H elimination and tautomerization cascade steps. The reaction tolerates a wide range of groups and produces valuable aminomethylenemalonates in high yields.
Co-reporter:Mi-Na Zhao, Le Yu, Nan-Fang Mo, Zhi-Hui Ren, Yao-Yu Wang and Zheng-Hui Guan
Inorganic Chemistry Frontiers 2017 - vol. 4(Issue 4) pp:
Publication Date(Web):
DOI:10.1039/C6QO00809G
Co-reporter:Hai-Tao Zhu, Ming-Jin Fan, De-Suo Yang, Xiao-Ling Wang, Sen Ke, Chao-Yang Zhang and Zheng-Hui Guan
Inorganic Chemistry Frontiers 2015 - vol. 2(Issue 5) pp:NaN509-509
Publication Date(Web):2015/03/13
DOI:10.1039/C5QO00048C
A facile and efficient iodine-promoted Meyer–Schuster rearrangement of propargyl alcohols for the synthesis of α-iodo-α,β-unsaturated ketones is presented. The reaction is concisely conducted at ambient temperature and shows good functional group tolerance.
Methanone, (5-methoxy-1-methyl-1H-indol-3-yl)phenyl-
Butyl 1-methyl-1h-indole-3-carboxylate
Imidazo[1,2-a]pyridine,2-(1,3-benzodioxol-5-yl)-
2-(5,6,7,8-Tetrahydro-2-naphthalenyl)imidazo[1,2-a]pyridine
2-(2,5-Dimethylphenyl)imidazo[1,2-a]pyridine
2-(2,4-Dimethylphenyl)imidazo[1,2-a]pyridine
1H-Pyrrole, 2,5-bis(4-bromophenyl)-3,4-dimethyl-
Benzamide, N-benzoyl-4-fluoro-
Ethanone, 1-(2,3,5-triphenyl-1H-pyrrol-1-yl)-
1-PROPANONE, 1-(4-FLUOROPHENYL)-, OXIME