Qiang Zhu

Find an error

Name:

Organization: Guangzhou Institutes of Biomedicine and Health

Department: State Key Laboratory of Respiratory Disease

Title:

TOPICS

Organic Chemistry

Hypervalent Iodine Amination

Chemicals
References

Palladium-Catalyzed Imidoylative Cyclization of Tryptophan-Derived Isocyanides: Access to β-Carbolines

Co-reporter:Shi Tang, Jian Wang, Zhuang Xiong, Zeqiang Xie, Dengke Li, Jinbo Huang, and Qiang Zhu

Organic Letters October 20, 2017 Volume 19(Issue 20) pp:5577-5577

Publication Date(Web):October 5, 2017

DOI:10.1021/acs.orglett.7b02725

A palladium-catalyzed imidoylative cyclization of ethyl-3-(1H-indol-3-yl)-2-isocyanopropanoates, derived from readily available tryptophan, to afford β-carboline derivatives has been developed. The reaction proceeds smoothly under mild conditions through sequential isocyanide insertion, intramolecular C–H imidoylation, and aerobic dehydrogenative aromatization with a decent substrate scope. This method provides a general approach for the synthesis of molecules containing the β-carboline fragment.

Denitrogenative Imidoyl Radical Cyclization: Synthesis of 2-Substituted Benzoimidazoles from 1-Azido-2-isocyanoarenes

Co-reporter:Dengke Li, Tingting Mao, Jinbo Huang, and Qiang Zhu

Organic Letters June 16, 2017 Volume 19(Issue 12) pp:

Publication Date(Web):June 5, 2017

DOI:10.1021/acs.orglett.7b01339

A novel access to 2-substituted benzoimidazoles, through unprecedented denitrogenative imidoyl radical cyclization of 1-azido-2-isocyanoarenes, has been developed. This tandem radical process was initiated by adding a C- or P-centered radical to isocyanide, followed by cycloaddition of the imidoyl radical to the azido group. Then, nitrogen loss and hydrogen abstraction of the resulting aminyl radical from surroundings delivered 2-substituted benzoimidazoles. Carbon radicals generated from another annulation process could also be applied, furnishing various heterocycle linked benzoimidazole derivatives.

Copper-catalyzed regioselective 1,2-thioamidation of alkenes

Co-reporter:Dengke Li;Tingting Mao;Jinbo Huang

Chemical Communications 2017 vol. 53(Issue 24) pp:3450-3453

Publication Date(Web):2017/03/21

DOI:10.1039/C7CC00083A

An efficient method for regioselective 1,2-thioamidation of terminal alkenes, catalyzed by copper in the presence of NFSI and thiols, has been disclosed. Under the reaction conditions, the amido radical was formed initially, followed by addition to the terminal carbon of alkenes and trapping of the resulting cuprate intermediate with thiols. Therefore, the regioselectivity was completely reversed compared to previously reported reactions which were initiated by sulfur-centred radicals or cations. When alkenes containing an amido N–H moiety were applied as substrates, intramolecular amido radical cyclization took place to afford sulfane substituted N-heterocycles.

Palladium-catalyzed C(sp2)–H aminoimidoylation of isocyano-containing arenes: synthesis of amino substituted N-heterocycles

Co-reporter:Zhuang Xiong;Jian Wang;Yanbo Wang;Shuang Luo

Organic Chemistry Frontiers 2017 vol. 4(Issue 9) pp:1768-1771

Publication Date(Web):2017/08/22

DOI:10.1039/C7QO00368D

An efficient access to amino substituted phenanthridine and isoquinoline derivatives, through palladium-catalyzed C(sp2)–H aminoimidoylation, has been developed. This process applies O-benzoyl hydroxylamines as oxidative amino sources to generate amino Pd(II) intermediates, followed by isocyanide insertion and intramolecular C(sp2)–H activation. Sequential C–N and C–C bond formation took place on isocyano-containing arenes in one step.

A one-pot synthesis of [1,2,3]triazolo[1,5-a]quinoxalines from 1-azido-2-isocyanoarenes with high bond-forming efficiency

Co-reporter:Dengke Li;Tingting Mao;Jinbo Huang

Chemical Communications 2017 vol. 53(Issue 7) pp:1305-1308

Publication Date(Web):2017/01/19

DOI:10.1039/C6CC08543A

An efficient approach to prepare 1,2,3-triazolo[1,5-a]quinoxaline scaffolds, starting from 1-azido-2-isocyanoarenes and terminal acetylenes or substituted acetaldehydes, has been developed. In the case of trifluoromethylation triggered cyclization, four chemical bonds, including two C–C and two C–N bonds, were formed consecutively without isolating the triazole intermediate. In addition, these triazo-fused products were readily transformed into diversified quinoxaline derivatives via rhodium-catalyzed carbenoid insertion reactions.

A metal-free synthesis of 2-aminobenzothiazoles through aminyl radical addition to aryl isothiocyanates

Co-reporter:Yimiao He, Jing Li, Shuang Luo, Jinbo Huang and Qiang Zhu

Chemical Communications 2016 vol. 52(Issue 54) pp:8444-8447

Publication Date(Web):08 Jun 2016

DOI:10.1039/C6CC04394A

A convenient synthesis of 2-aminobenzothiazoles, starting from aryl isothiocyanates and formamides under metal-free conditions, is described. Various secondary and tertiary amine- and even α-amino acid-derived formamides can be used as amino sources in this process. Mechanistic studies suggest that the reaction is initiated by decarbonylative aminyl radical formation in the presence of n-Bu4NI and TBHP, followed by aminyl radical addition to isothiocyanates and cyclization via sulfur centred radical intermediates.

Copper-mediated C(sp3)–H azidation with Me3SiN3: synthesis of imidazoles from ketones and aldehydes

Co-reporter:Zeqiang Xie, Jiaojiao Deng, Zhiping Qiu, Juan Li and Qiang Zhu

Chemical Communications 2016 vol. 52(Issue 38) pp:6467-6470

Publication Date(Web):18 Apr 2016

DOI:10.1039/C6CC01863G

The efficient construction of 2,4,5-trisubstituted imidazoles, through a copper-mediated three-component reaction involving ketones, aldehydes, and Me3SiN3, has been developed. During the process, 4 C–N bonds were formed sequentially. Experimental results and DFT calculations suggested that azidation of the alpha methylene group of the ketone was the key C–N bond-forming step.

Intramolecular Imidoylative Heck Reaction: Synthesis of Cyclic Ketoimines from Functionalized Isocyanide

Co-reporter:Jian Wang, Shi Tang, and Qiang Zhu

Organic Letters 2016 Volume 18(Issue 13) pp:3074-3077

Publication Date(Web):June 15, 2016

DOI:10.1021/acs.orglett.6b01174

Efficient access to five- to seven-membered cyclic ketoimines, through palladium-catalyzed intramolecular imidoylative Heck reaction of alkene-containing isocyanides, has been developed. Consecutive isocyanide and alkene insertion into aryl or alkyl Pd(II) intermediates takes place in this process. No byproduct derived from monoinsertion or reversed sequence is detected.

Recent progress in imidoyl radical-involved reactions

Co-reporter:Jian Lei, Jinbo Huang and Qiang Zhu

Organic & Biomolecular Chemistry 2016 vol. 14(Issue 9) pp:2593-2602

Publication Date(Web):05 Feb 2016

DOI:10.1039/C6OB00087H

Much attention has been paid to imidoyl radical-involved reactions in recent years. As a divergent reactive intermediate, imidoyl radicals are used for the synthesis of functionalized heterocycles, nitriles, imines, amines, etc. This review is intended to highlight some recent progress in the past decade.

Surface Confined Retro Diels–Alder Reaction Driven by the Swelling of Weak Polyelectrolytes

Co-reporter:Beier Lyu, Wenli Cha, Tingting Mao, Yuanzi Wu, Hujun Qian, Yitian Zhou, Xiuli Chen, Shen Zhang, Lanying Liu, Guang Yang, Zhongyuan Lu, Qiang Zhu, and Hongwei Ma

ACS Applied Materials & Interfaces 2015 Volume 7(Issue 11) pp:6254

Publication Date(Web):March 3, 2015

DOI:10.1021/acsami.5b00538

Recently, the type of reactions driven by mechanical force has increased significantly; however, the number of methods for activating those mechanochemical reactions stays relatively limited. Furthermore, in situ characterization of a reaction is usually hampered by the inherent properties of conventional methods. In this study, we report a new platform that utilizes mechanical force generated by the swelling of surface tethered weak polyelectrolytes. An initiator with Diels–Alder (DA) adduct structure was applied to prepare the polyelectrolyte-carboxylated poly(OEGMA-r-HEMA), so that the force could trigger the retro DA reaction. The reaction was monitored in real time by quartz crystal microbalance and confirmed with atomic force microscopy and X-ray photoelectron spectroscopy. Compared with the conventional heating method, the swelling-induced retro DA reaction proceeded rapidly with high conversion ratio and selectivity. A 23.61 kcal/mol theoretical energy barrier supported the practicability of this retro DA reaction being triggered mechanically at ambient temperature. During swelling, the tensile force was controllable and persistent. This unique feature imparts this mechanochemical platform the potential to “freeze” an intermediate state of a reaction for in situ spectroscopic observations, such as surface-enhanced Raman spectroscopy and frequency generation spectroscopy.Keywords: mechanochemistry; polyelectrolyte; polymer brush; quartz crystal microbalance; retro Diels−Alder reaction

Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[d]imidazothiazoles

Co-reporter:Jian Wang, Jing Li, and Qiang Zhu

Organic Letters 2015 Volume 17(Issue 21) pp:5336-5339

Publication Date(Web):October 28, 2015

DOI:10.1021/acs.orglett.5b02694

A tunable route to both isomers of benzo[d]imidazothiazole has been developed through copper-promoted cycloaddition of α-methylenyl isocyanides with benzothiazoles. When the C2 position of benzothiazole is linked to a C–H or C–C bond, benzo[d]imidazo[2,1-b]thiazoles are obtained through a novel rearrangement via C–S bond cleavage and formation of a new C–S bond. When 2-chloro- or 2-bromobenzothiazoles are used under the same reaction conditions, the isomeric benzo[d]imidazo[5,1-b]thiazoles are formed selectively. These reactions proceed smoothly in moderate to excellent yields at room temperature, and a wide range of functional groups are tolerated.

Copper-Catalyzed Trifluoromethylalkynylation of Isocyanides

Co-reporter:Jian Lei, Xiaoxing Wu, and Qiang Zhu

Organic Letters 2015 Volume 17(Issue 10) pp:2322-2325

Publication Date(Web):April 23, 2015

DOI:10.1021/acs.orglett.5b00730

The title reaction proceeds with acetylenic triflones and isocyanides under mild conditions using copper as a catalyst. This transformation provides an efficient access to (E)-N-alkyl trifluoromethyl alkynyl ketoimines, which are useful building blocks for the synthesis of CF3-containing N-heterocycles, propargylamines, etc.

Aminopalladation-Triggered Carbene Insertion Reaction: Synthesis of 2-(1H-Indol-3-yl)acetates

Co-reporter:Ziwei Hu;Shuang Luo

Advanced Synthesis & Catalysis 2015 Volume 357( Issue 5) pp:1060-1064

Publication Date(Web):

DOI:10.1002/adsc.201400799

A Facile Synthesis of Pyrazoles through Metal-Free Oxidative C(sp2)H Cycloamination of Vinyl Hydrazones

Co-reporter:Dr. Dongdong Liang ; Qiang Zhu

Asian Journal of Organic Chemistry 2015 Volume 4( Issue 1) pp:42-45

Publication Date(Web):

DOI:10.1002/ajoc.201402254

Abstract

An efficient synthesis of structurally diversified pyrazole derivatives through metal-free oxidative CH cycloamination of vinyl hydrazones has been developed. The reaction was usually complete within 5 min at ambient temperature in air in good to excellent yields.

Palladium-Catalyzed Intramolecular C(sp2)-H Imidoylation for the Synthesis of Six-Membered N-Heterocycles

Co-reporter:Jing Li, Yimiao He, Shuang Luo, Jian Lei, Jian Wang, Zeqiang Xie, and Qiang Zhu

The Journal of Organic Chemistry 2015 Volume 80(Issue 4) pp:2223-2230

Publication Date(Web):January 22, 2015

DOI:10.1021/jo502731n

A new strategy for the construction of phenanthridine and isoquinoline scaffolds, starting from arenes containing a pending isocyanide moiety under palladium catalysis, has been developed. This process involves sequential intermolecular isocyanide insertion to an aryl palladium(II) intermediate and intramolecular aromatic C–H activation as key steps. Alkyl palladium(II) intermediate lacking β-hydrogen is also applicable to this reaction, generating unique bisheterocyclic scaffolds with three C–C bonds being formed consecutively.

Palladium-catalyzed intermolecular C-H amidation of indoles with sulfonyl azides

Co-reporter:Ziwei Hu;Shuang Luo

Science China Chemistry 2015 Volume 58( Issue 8) pp:1349-1353

Publication Date(Web):2015 August

DOI:10.1007/s11426-015-5369-y

A new kind of intermolecular indole C-H amidation reaction catalyzed by the most frequently used palladium catalyst has been developed. Sulfonyl azide was employed as an innovative nitrogen source and environmentally benign nitrogen was produced as the only byproduct.

Arylative Cyclization of 2-Isocyanobiphenyls with Anilines: One-Pot Synthesis of 6-Arylphenanthridines via Competitive Reaction Pathways

Co-reporter:Zhonghua Xia, Jinbo Huang, Yimiao He, Jiaji Zhao, Jian Lei, and Qiang Zhu

Organic Letters 2014 Volume 16(Issue 9) pp:2546-2549

Publication Date(Web):April 22, 2014

DOI:10.1021/ol500923t

A transition-metal-free method for the synthesis of C6 phenanthridine derivatives by arylative cyclization of 2-isocyanobiphenyls with arylamines in one pot was developed. Mechanistic studies suggest that electrophilic aromatic substitution (SEAr) of a nitrilium intermediate and homolytic aromatic substitution (HAS) of an imidoyl radical intermediate are two competitive reaction pathways involved in the annulation step.

Palladium-Catalyzed C(sp2)–H Pyridocarbonylation of N-Aryl-2-aminopyridines: Dual Function of the Pyridyl Moiety

Co-reporter:Dongdong Liang, Yimiao He, and Qiang Zhu

Organic Letters 2014 Volume 16(Issue 10) pp:2748-2751

Publication Date(Web):May 7, 2014

DOI:10.1021/ol501070g

An efficient synthesis of 11H-pyrido[2,1-b]quinazolin-11-one through palladium-catalyzed C(sp2)–H pyridocarbonylation of N-aryl-2-aminopyridines has been developed. The pyridyl group acts as an intramolecular nucleophile for the first time in C–H carbonylation reactions.

Copper-Catalyzed C(sp2)–H Amidation with Azides as Amino Sources

Co-reporter:Jiangling Peng, Zeqiang Xie, Ming Chen, Jian Wang, and Qiang Zhu

Organic Letters 2014 Volume 16(Issue 18) pp:4702-4705

Publication Date(Web):September 5, 2014

DOI:10.1021/ol502010g

A copper-catalyzed C–H amidation process, with azides as amino sources under oxidant-free conditions, has been developed. When N-heterocycles were employed as directing groups, sulfonylazide and benzoylazide could be used as amidating reagents to provide corresponding N-arylamides. When amidines or imine were used, tandem C–N/N–N bond formation occurred to afford indazole derivatives in one pot.

Copper-Catalyzed Intramolecular Oxidative C(sp3)H Amidation of 2-Aminoacetophenones: Efficient Synthesis of Indoline-2,3-diones

Co-reporter:Jinbo Huang;Tingting Mao

European Journal of Organic Chemistry 2014 Volume 2014( Issue 14) pp:2878-2882

Publication Date(Web):

DOI:10.1002/ejoc.201400012

Abstract

An efficient synthesis of diverse indoline-2,3-diones from 2-aminoacetophenones through copper-catalyzed intramolecular C(sp³)–H amidation is developed. The reaction proceeds in DMSO by using O₂ as the sole oxidant to provide the desired products in moderate to good yields.

Palladium-Catalyzed Imidoylative Cyclization of -Isocyanoacetamides: Efficient Access to C2-Diversified Oxazoles

Co-reporter:Jian Wang;Shuang Luo;Jinbo Huang;Tingting Mao

Chemistry - A European Journal 2014 Volume 20( Issue 35) pp:11220-11224

Publication Date(Web):

DOI:10.1002/chem.201403033

Abstract

A novel procedure for the synthesis of C2-diversified oxazoles, through palladium-catalyzed imidoylative cyclization of α-isocyanoacetamides with aryl, vinyl, alkynyl halides, or triflates, was developed. Migratory insertion of isocyanide into a C-palladium(II) intermediate in a cascade process was also realized, generating alkyl-substituted oxazoles. Therefore, oxazoles functionalized at the C2 position with sp, sp², and sp³ hybridized carbon atoms are accessible by applying this method.

A Transition-Metal-Free Synthesis of Arylcarboxyamides from Aryl Diazonium Salts and Isocyanides

Co-reporter:Zhonghua Xia and Qiang Zhu

Organic Letters 2013 Volume 15(Issue 16) pp:4110-4113

Publication Date(Web):August 6, 2013

DOI:10.1021/ol4017244

A transition-metal-free carboxyamidation process, using aryl diazonium tetrafluoroborates and isocyanides under mild conditions, has been developed. This novel conversion was initiated by a base and solvent induced aryl radical, followed by radical addition to isocyanide and single electron transfer (SET) oxidation, affording the corresponding arylcarboxyamide upon hydration of the nitrilium intermediate.

A Metal-Free Tandem Demethylenation/C(sp2)–H Cycloamination Process of N-Benzyl-2-aminopyridines via C–C and C–N Bond Cleavage

Co-reporter:Dongdong Liang, Yimiao He, Lanying Liu, and Qiang Zhu

Organic Letters 2013 Volume 15(Issue 13) pp:3476-3479

Publication Date(Web):June 26, 2013

DOI:10.1021/ol4015656

A mild, metal-free synthesis of pyrido[1,2-a]benzimidazoles starting with N-benzyl-2-aminopyridines, which employs PhI(OPiv)2 as a stoichiometric oxidant, has been developed. The process is initiated by an unusual PhI(OPiv)2-mediated ipso SEAr reaction, followed by solvent-assisted C–C and C–N bond cleavage.

C–H cycloamination of N-aryl-2-aminopyridines and N-arylamidines catalyzed by an in situ generated hypervalent iodine(III) reagent

Co-reporter:Yimiao He, Jinbo Huang, Dongdong Liang, Lanying Liu and Qiang Zhu

Chemical Communications 2013 vol. 49(Issue 66) pp:7352-7354

Publication Date(Web):24 Jun 2013

DOI:10.1039/C3CC43784A

A metal-free synthesis of diversified pyrido[1,2-a]benzimidazoles and 1H-benzo[d]imidazoles from N-aryl-2-aminopyridines and N-arylamidines has been developed. The C–H cycloamination reaction was catalyzed by hypervalent iodine(III) species generated in situ from iodobenzene (catalytic) and peracetic acid (stoichiometric). The reaction proceeded smoothly at ambient temperature to provide the corresponding N-heterocycles in good to excellent yields.

Synthesis of phenanthridinones via palladium-catalyzed C(sp2)–H aminocarbonylation of unprotected o-arylanilines

Co-reporter:Dongdong Liang, Ziwei Hu, Jiangling Peng, Jinbo Huang and Qiang Zhu

Chemical Communications 2013 vol. 49(Issue 2) pp:173-175

Publication Date(Web):05 Nov 2012

DOI:10.1039/C2CC36817J

An efficient synthesis of free (NH)-phenanthridinones through Pd-catalyzed C(sp2)–H aminocarbonylation of unprotected o-arylanilines under an atmospheric pressure of CO has been developed. Some ortho heteroarene substituted anilines as well as N-alkyl protected o-arylanilines are also suitable substrates for this C–H aminocarbonylation reaction.

Synthesis of 1H-Indole-3-carboxamidines through a Palladium-Catalyzed Three-Component Reaction Involving Isocyanide Insertion as a Key Step

Co-reporter:Ziwei Hu;Jian Wang;Dongdong Liang

Advanced Synthesis & Catalysis 2013 Volume 355( Issue 16) pp:3290-3294

Publication Date(Web):

DOI:10.1002/adsc.201300532

Synthesis of 10-Methylacridin-9(10H)-ones through Cu-Catalyzed Intramolecular Oxidative C(sp2)H Amination of 2-(Methylamino)benzophenones

Co-reporter:Jinbo Huang;Congqing Wan;Ming-Fang Xu

European Journal of Organic Chemistry 2013 Volume 2013( Issue 10) pp:1876-1880

Publication Date(Web):

DOI:10.1002/ejoc.201201748

Abstract

An efficient synthesis of a diverse set of 10-methylacridin-9(10H)-ones from 2-(methylamino)benzophenones has been developed. The reaction proceeds though Cu-catalyzed intramolecular aromatic C–H amination by using O₂ as the sole oxidant to provide the desired products in moderate to good yields. In addition, 2-allylamino- and 2-(benzylamino)benzophenones as well as unprotected substrates can also undergo the C–H amination reaction to deliver the corresponding cyclization products smoothly. Preliminary mechanistic studies suggest that C–H activation is involved in a rate-limiting step.

Palladium-catalyzed cyclization of o-alkynyltrifluoroacetanilides followed by isocyanide insertion: synthesis of 2-substituted 1H-indole-3-carboxamides

Co-reporter:Ziwei Hu, Dongdong Liang, Jiaji Zhao, Jinbo Huang and Qiang Zhu

Chemical Communications 2012 vol. 48(Issue 59) pp:7371-7373

Publication Date(Web):13 Jun 2012

DOI:10.1039/C2CC33435F

A base-controlled synthesis of 2-substituted secondary and tertiary 1H-indole-3-carboxamides through PdCl2-catalyzed cyclization of o-alkynyltrifluoroacetanilides followed by isocyanide insertion has been developed. The reaction proceeds smoothly at ambient temperature using O2 in air as the sole oxidant of the palladium catalyst.

Palladium-Catalyzed C(sp2)–H Cyanation Using Tertiary Amine Derived Isocyanide as a Cyano Source

Co-reporter:Jiangling Peng, Jiaji Zhao, Ziwei Hu, Dongdong Liang, Jinbo Huang, and Qiang Zhu

Organic Letters 2012 Volume 14(Issue 18) pp:4966-4969

Publication Date(Web):August 31, 2012

DOI:10.1021/ol302372p

An unprecedented palladium-catalyzed cyanation of aromatic C–H bonds by using tertiary amine derived isocyanide as a novel cyano source was developed. Cu(TFA)2 was used as a requisite stoichiometric oxidant. Mechanistic studies suggest that a tertiary carbon cation-based intermediate is involved following the C–N bond breakage.

Direct carboxamidation of indoles by palladium-catalyzed C–H activation and isocyanide insertion

Co-reporter:Jiangling Peng, Lanying Liu, Ziwei Hu, Jinbo Huang and Qiang Zhu

Chemical Communications 2012 vol. 48(Issue 31) pp:3772-3774

Publication Date(Web):20 Feb 2012

DOI:10.1039/C2CC30351E

A selective C3 carboxamidation of indoles including free (N–H) ones by palladium-catalyzed sequential C–H activation–isocyanide insertion has been developed.

CuI-Mediated Sequential Iodination/Cycloetherification of o-Arylphenols: Synthesis of 2- or 4-Iododibenzofurans and Mechanistic Studies

Co-reporter:Jiaji Zhao, Qi Zhang, Lanying Liu, Yimiao He, Jing Li, Juan Li, and Qiang Zhu

Organic Letters 2012 Volume 14(Issue 20) pp:5362-5365

Publication Date(Web):October 2, 2012

DOI:10.1021/ol302562a

An efficient synthesis of 2- or 4-iododibenzofurans through CuI-mediated sequential iodination/cycloetherification of two aromatic C–H bonds in o-arylphenols has been developed. Both the preexisting electron-withdrawing groups (NO2, CN, and CHO) and the newly introduced iodide are readily modified for a focused dibenzofuran library synthesis. Mechanistic studies and DFT calculations suggest that a Cu(III)-mediated rate-limiting C–H activation step is involved in cycloetherification.

Cu-Catalyzed Oxidative C(sp2)–H Cycloetherification of o-Arylphenols for the Preparation of Dibenzofurans

Co-reporter:Jiaji Zhao, Yong Wang, Yimiao He, Lanying Liu, and Qiang Zhu

Organic Letters 2012 Volume 14(Issue 4) pp:1078-1081

Publication Date(Web):January 30, 2012

DOI:10.1021/ol203442a

A new process involving copper-catalyzed aerobic C(sp2)–H activation, followed by cycloetherification, has been developed. This reaction serves as a direct method for the preparation of multisubstituted dibenzofurans starting with o-arylphenols. The presence of a strong para-electron-withdrawing group (e.g., NO2) on the phenol is essential for the success of the reaction.

Palladium(II)-Catalyzed Cycloamidination via C(sp2)H Activation and Isocyanide Insertion

Co-reporter:Yong Wang

Advanced Synthesis & Catalysis 2012 Volume 354( Issue 10) pp:1902-1908

Publication Date(Web):

DOI:10.1002/adsc.201200106

Abstract

An efficient method for the synthesis of nitrogen heterocycles containing a cyclic amidine moiety has been developed. The process involves palladium-catalyzed C(sp²)H activation and isocyanide insertion starting with readily accessible ortho-heteroarene-substituted aniline derivatives under mild conditions.

Synthesis of Benzimidazoles by PIDA-Promoted Direct C(sp2)H Imidation of N-Arylamidines

Co-reporter:Dr. Jinbo Huang;Yimiao He;Yong Wang ;Dr. Qiang Zhu

Chemistry - A European Journal 2012 Volume 18( Issue 44) pp:13964-13967

Publication Date(Web):

DOI:10.1002/chem.201202271

Copper-Catalyzed Intramolecular Dehydrogenative Aminooxygenation: Direct Access to Formyl-Substituted Aromatic N-Heterocycles

Co-reporter:Honggen Wang;Yong Wang;Dongdong Liang;Lanying Liu;Dr. Jiancun Zhang;Dr. Qiang Zhu

Angewandte Chemie International Edition 2011 Volume 50( Issue 25) pp:5678-5681

Publication Date(Web):

DOI:10.1002/anie.201100362

Copper-Catalyzed Intramolecular Dehydrogenative Aminooxygenation: Direct Access to Formyl-Substituted Aromatic N-Heterocycles

Co-reporter:Honggen Wang;Yong Wang;Dongdong Liang;Lanying Liu;Dr. Jiancun Zhang;Dr. Qiang Zhu

Angewandte Chemie 2011 Volume 123( Issue 25) pp:5796-5799

Publication Date(Web):

DOI:10.1002/ange.201100362

Synthesis of Quinazolin-4(3H)-ones via Pd(II)-Catalyzed Intramolecular C(sp2)–H Carboxamidation of N-arylamidines

Co-reporter:Bin Ma, Yong Wang, Jiangling Peng, and Qiang Zhu

The Journal of Organic Chemistry 2011 Volume 76(Issue 15) pp:6362-6366

Publication Date(Web):June 15, 2011

DOI:10.1021/jo2007362

An efficient synthesis of quinazolin-4(3H)-ones from N-arylamidines, through palladium-catalyzed intramolecular C(sp2)–H carboxamidation, has been developed. The reaction, carried out in the presence of 1.0 equiv of CuO as oxidant under atmospheric pressure of CO, provides diversified 2-aryl(alkyl)quinazolin-4(3H)-ones in reasonable to good yields from N-arylamidines, which are readily derived from anilines and nitriles. Compared with existing approaches to quinazolin-4(3H)-ones, the current strategy features atom-economy and step-efficiency.

p-Toluenesulfonic Acid Promoted Annulation of 2-Alkynylanilines with Activated Ketones: Efficient Synthesis of 4-Alkyl-2,3-Disubstituted Quinolines

Co-reporter:Changlan Peng;Yong Wang;Lanying Liu;Honggen Wang;Jiaji Zhao

European Journal of Organic Chemistry 2010 Volume 2010( Issue 5) pp:818-822

Publication Date(Web):

DOI:10.1002/ejoc.200901257

Abstract

Reactions between readily available 2-alkynylanilines and activated ketones such as β-keto esters promoted by p-toluenesulfonic acid afford 4-alkyl-2,3-disubstituted quinolines in good to excellent yields. The generality of substituents at the other end of the triple bond of 2-alkynylanilines makes the method a valuable approach to diversified 4-alkylquinolines, which are difficult to obtain by classical methods such as the Friedländer reaction. Quinoline dimers can be prepared efficiently with alkyl or aryl linkers at C-4.

Structure-based design, synthesis and biological evaluation of new N-carboxyphenylpyrrole derivatives as HIV fusion inhibitors targeting gp41

Co-reporter:Yong Wang, Hong Lu, Qiang Zhu, Shibo Jiang, Yun Liao

Bioorganic & Medicinal Chemistry Letters 2010 Volume 20(Issue 1) pp:189-192

Publication Date(Web):1 January 2010

DOI:10.1016/j.bmcl.2009.10.139

A new series of N-carboxyphenylpyrrole ligands were designed using GeometryFit based on an X-ray crystal structure of gp41. The synthesized ligands showed significant inhibitory activities against HIV gp41 6-helix bundle formation, HIV-1 mediated cell–cell fusion and HIV-1 replication.A new series of N-carboxyphenylpyrrole ligands were designed using GeometryFit based on an X-ray crystal structure of gp41. The synthesized ligands showed significant inhibitory activities against HIV gp41 6-helix bundle formation, HIV-1 mediated cell-cell fusion and HIV-1 replication.

Tetrabutylammonium chloride-triggered 6-endo cyclization of o-alkynylisocyanobenzenes: an efficient synthesis of 2-chloro-3-substituted quinolines

Co-reporter:Lanying Liu, Yong Wang, Honggen Wang, Changlan Peng, Jiaji Zhao, Qiang Zhu

Tetrahedron Letters 2009 50(48) pp: 6715-6719

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.09.096

An efficient synthesis of 4-alkyl-2(1H)-quinazolinones and 4-alkyl-2-chloroquinazolines from 1-(2-alkynylphenyl)ureas

Co-reporter:Honggen Wang, Lanying Liu, Yong Wang, Changlan Peng, Jiancun Zhang, Qiang Zhu

Tetrahedron Letters 2009 50(49) pp: 6841-6843

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.09.130

Sulfuric acid promoted condensation cyclization of 2-(2-(trimethylsilyl) ethynyl)anilines with arylaldehydes in alcoholic solvents: an efficient one-pot synthesis of 4-alkoxy-2-arylquinolines

Co-reporter:Yong Wang, Changlan Peng, Lanying Liu, Jiaji Zhao, Li Su, Qiang Zhu

Tetrahedron Letters 2009 50(19) pp: 2261-2265

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.02.206

Recent progress in imidoyl radical-involved reactions

Co-reporter:Jian Lei, Jinbo Huang and Qiang Zhu

Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 9) pp:NaN2602-2602

Publication Date(Web):2016/02/05

DOI:10.1039/C6OB00087H

Copper-mediated C(sp3)–H azidation with Me3SiN3: synthesis of imidazoles from ketones and aldehydes

Co-reporter:Zeqiang Xie, Jiaojiao Deng, Zhiping Qiu, Juan Li and Qiang Zhu

Chemical Communications 2016 - vol. 52(Issue 38) pp:NaN6470-6470

Publication Date(Web):2016/04/18

DOI:10.1039/C6CC01863G

Direct carboxamidation of indoles by palladium-catalyzed C–H activation and isocyanide insertion

Co-reporter:Jiangling Peng, Lanying Liu, Ziwei Hu, Jinbo Huang and Qiang Zhu

Chemical Communications 2012 - vol. 48(Issue 31) pp:NaN3774-3774

Publication Date(Web):2012/02/20

DOI:10.1039/C2CC30351E

A selective C3 carboxamidation of indoles including free (N–H) ones by palladium-catalyzed sequential C–H activation–isocyanide insertion has been developed.

C–H cycloamination of N-aryl-2-aminopyridines and N-arylamidines catalyzed by an in situ generated hypervalent iodine(III) reagent

Co-reporter:Yimiao He, Jinbo Huang, Dongdong Liang, Lanying Liu and Qiang Zhu

Chemical Communications 2013 - vol. 49(Issue 66) pp:NaN7354-7354

Publication Date(Web):2013/06/24

DOI:10.1039/C3CC43784A

Synthesis of phenanthridinones via palladium-catalyzed C(sp2)–H aminocarbonylation of unprotected o-arylanilines

Co-reporter:Dongdong Liang, Ziwei Hu, Jiangling Peng, Jinbo Huang and Qiang Zhu

Chemical Communications 2013 - vol. 49(Issue 2) pp:NaN175-175

Publication Date(Web):2012/11/05

DOI:10.1039/C2CC36817J

Palladium-catalyzed cyclization of o-alkynyltrifluoroacetanilides followed by isocyanide insertion: synthesis of 2-substituted 1H-indole-3-carboxamides

Co-reporter:Ziwei Hu, Dongdong Liang, Jiaji Zhao, Jinbo Huang and Qiang Zhu

Chemical Communications 2012 - vol. 48(Issue 59) pp:NaN7373-7373

Publication Date(Web):2012/06/13

DOI:10.1039/C2CC33435F

Copper-mediated C(sp2)–H amination using TMSN3 as a nitrogen source: redox-neutral access to primary anilines

Co-reporter:Jiangling Peng, Ming Chen, Zeqiang Xie, Shuang Luo and Qiang Zhu

Inorganic Chemistry Frontiers 2014 - vol. 1(Issue 7) pp:

Publication Date(Web):

DOI:10.1039/C4QO00143E

Copper-mediated C(sp3)–H amination in a multiple C–N bond-forming strategy for the synthesis of N-heterocycles

Co-reporter:Zeqiang Xie, Jiangling Peng and Qiang Zhu

Inorganic Chemistry Frontiers 2016 - vol. 3(Issue 1) pp:NaN86-86

Publication Date(Web):2015/11/20

DOI:10.1039/C5QO00313J

An efficient construction of imidazo[1,5-a]pyridines, through a three-component reaction involving benzyl substituted pyridines, aldehydes, and TMSN3, has been developed. Three C–N bonds were formed in one pot. Copper-promoted amination of the benzylic C(sp3)–H bond is a key step of this multiple C–N bond-forming sequence.

A room-temperature synthesis of 2,2′-bisoxazoles through palladium-catalyzed oxidative coupling of α-isocyanoacetamides

Co-reporter:Jian Wang, Shuang Luo, Jing Li and Qiang Zhu

Inorganic Chemistry Frontiers 2014 - vol. 1(Issue 11) pp:NaN1288-1288

Publication Date(Web):2014/11/05

DOI:10.1039/C4QO00250D

A palladium-catalyzed synthesis of symmetric and unsymmetric 2,2′-bisoxazoles starting from readily available α-isocyanoacetamides was developed. The reaction was performed at room temperature in air which acted as the sole oxidant of Pd(0). Mechanistic studies suggested that double isocyanide insertion into the Pd(II)–O bond was involved.

A metal-free synthesis of 2-aminobenzothiazoles through aminyl radical addition to aryl isothiocyanates

Co-reporter:Yimiao He, Jing Li, Shuang Luo, Jinbo Huang and Qiang Zhu

Chemical Communications 2016 - vol. 52(Issue 54) pp:NaN8447-8447

Publication Date(Web):2016/06/08

DOI:10.1039/C6CC04394A

Copper-catalyzed regioselective 1,2-thioamidation of alkenes

Co-reporter:Dengke Li, Tingting Mao, Jinbo Huang and Qiang Zhu

Chemical Communications 2017 - vol. 53(Issue 24) pp:NaN3453-3453

Publication Date(Web):2017/02/28

DOI:10.1039/C7CC00083A

A one-pot synthesis of [1,2,3]triazolo[1,5-a]quinoxalines from 1-azido-2-isocyanoarenes with high bond-forming efficiency

Co-reporter:Dengke Li, Tingting Mao, Jinbo Huang and Qiang Zhu