Co-reporter:Xinwei Hu, Xun Chen, Yong Zhu, Yuanfu Deng, Huaqiang Zeng, Huanfeng Jiang, and Wei Zeng
Organic Letters July 7, 2017 Volume 19(Issue 13) pp:
Publication Date(Web):June 16, 2017
DOI:10.1021/acs.orglett.7b01372
A Rh(III)-catalyzed carboamination of alkynyl cycloalkanols with arylamines has been developed. This transformation involves a novel Csp2–H/Csp3–Csp3 activation relay and provides an efficient approach to versatile 1,2,3-trisubstituted indoles with a broad range of functional group tolerance.
Co-reporter:Siyi Bai;Xun Chen;Xinwei Hu;Yuanfu Deng;Huanfeng Jiang
Organic & Biomolecular Chemistry 2017 vol. 15(Issue 17) pp:3638-3647
Publication Date(Web):2017/05/03
DOI:10.1039/C7OB00367F
An Ir(III)-catalyzed relay aryl C–H bond carbenoid insertion cascade of N-aryl-2-pyridinamines with diazo Meldrum's acid has been developed. This method provides an efficient approach to multifunctionalized 1,3-dihydroindol-2-ones with a broad range of functional group tolerance. Furthermore, this protocol could be applied for the concise synthesis of bioactive hematopoietic growth factor analogues.
Co-reporter:Zhenhui Zhang;Kunkun Liu;Xun Chen;Shi-Jian Su;Yuanfu Deng
RSC Advances (2011-Present) 2017 vol. 7(Issue 49) pp:30554-30558
Publication Date(Web):2017/06/13
DOI:10.1039/C7RA04889K
A rhodium(III)-catalyzed indole-directed aryl C–H bond carbenoid insertion cascade of 2-arylindoles with diazo compounds has been developed. This method provides a rapid access to 1,2-benzocarbazoles and isoquinoline-based polycyclic heteroaromatics with a broad range of functional group tolerance. The primary evaluation of the photoluminescence property of the novel extended π-systems indicated that these heteroarenes could be potentially used in the field of optoelectronic materials.
Co-reporter:Ying Xie, Xun Chen, Xin Liu, Shi-Jian Su, Jianzhang Li and Wei Zeng
Chemical Communications 2016 vol. 52(Issue 34) pp:5856-5859
Publication Date(Web):29 Mar 2016
DOI:10.1039/C6CC00254D
A novel Rh(III)-catalyzed relay cross-coupling/cyclization cascade between arylketoimines and diazoesters is described. This transformation provides a concise access to unique π-conjugated 1-azaphenalenes (1-APLEs) via a double aryl Csp2–H bond carbenoid functionalization process. As illustrative examples, the 1-APLE-based π-conjugated molecules which possess low-lying HOMO levels could be converted to promising organic optoelectronic materials.
Co-reporter:Xun Chen, Xinwei Hu, Yuanfu Deng, Huanfeng Jiang, and Wei Zeng
Organic Letters 2016 Volume 18(Issue 18) pp:4742-4745
Publication Date(Web):September 1, 2016
DOI:10.1021/acs.orglett.6b02421
A Co(III)-catalyzed [4 + 1] cycloaddition of 2-arylpyridines or 2-alkenylpyridines with aldehydes through Csp2–H bond activation has been developed. This protocol provides a facile approach to structurally diverse indolizines including benzoindolizines with a broad range of functional group tolerance.
Co-reporter:Tengfei Chen, Xun Chen, Jun Wei, Dongen Lin, Ying Xie, and Wei Zeng
Organic Letters 2016 Volume 18(Issue 9) pp:2078-2081
Publication Date(Web):April 25, 2016
DOI:10.1021/acs.orglett.6b00709
A copper-catalyzed cycloamination of α-Csp3–H bond of N-aryl ketimines with sodium azide has been developed. This methodology provides an efficient access to quinoxalines and features mild reaction conditions and readily available ketimines with diverse functional group tolerance.
Co-reporter:Xun Chen; Xinwei Hu; Siyi Bai; Yuanfu Deng; Huanfeng Jiang
Organic Letters 2016 Volume 18(Issue 2) pp:192-195
Publication Date(Web):December 28, 2015
DOI:10.1021/acs.orglett.5b03231
The Rh(III)-catalyzed regioselective C2–H bond carbenoid insertion/cyclization of N-amidoindoles with α-acyl diazo compounds has been developed. This method provides a novel approach to 2H-pyrimido[1,6-a]indol-1-ones with a broad range of functional group tolerance. The synthetic utilities of the approach are demonstrated by versatile chemical transformations.
Co-reporter:Xinsheng Xiao;Wei Zhang;Xiaoxia Lu;Yuanfu Deng;Huangfeng Jiang
Advanced Synthesis & Catalysis 2016 Volume 358( Issue 15) pp:2497-2509
Publication Date(Web):
DOI:10.1002/adsc.201600248
Co-reporter:Jun Wei, Jingxing Jiang, Xinsheng Xiao, Dongen Lin, Yuanfu Deng, Zhuofeng Ke, Huanfeng Jiang, and Wei Zeng
The Journal of Organic Chemistry 2016 Volume 81(Issue 3) pp:946-955
Publication Date(Web):January 8, 2016
DOI:10.1021/acs.joc.5b02509
Copper(I)-catalyzed 5-sulfonation of quinolines via bidentate-chelation assistance has been developed. The reaction is compatible with a wide range of quinoline substrates and arylsulfonyl chlorides. Experimental and theoretical (DFT) investigation implicated that a single-electron-transfer process is involved in this sulfonylation transformation.
Co-reporter:Shaomin Fu, Honghao Yang, Guoqiang Li, Yuanfu Deng, Huanfeng Jiang, and Wei Zeng
Organic Letters 2015 Volume 17(Issue 4) pp:1018-1021
Publication Date(Web):February 10, 2015
DOI:10.1021/acs.orglett.5b00131
The first Cu(II)-catalyzed highly enantioselective intramolecular cyclization of N-alkenylureas was developed for the concise assembly of chiral vicinal diamino bicyclic heterocycles. Facile removal of carbonyl group of the carbamido moiety allowed for ready access to enantioenriched cyclic vicinal diamines.
Co-reporter:Wei Zhang, Jun Wei, Shaomin Fu, Dongen Lin, Huanfeng Jiang, and Wei Zeng
Organic Letters 2015 Volume 17(Issue 6) pp:1349-1352
Publication Date(Web):March 6, 2015
DOI:10.1021/ol503618m
A carboamide-directed ruthenium-catalyzed C2-hydroindolation of alkynes has been described. This transformation provides a rapid access to free (N–H) C2-syn-alkenylated indole derivatives with the assistance of copper(II) salts, in which the directing group is removed via a one-pot process.
Co-reporter:Xun Chen, Ying Xie, Xinsheng Xiao, Guoqiang Li, Yuanfu Deng, Huanfeng Jiang and Wei Zeng
Chemical Communications 2015 vol. 51(Issue 83) pp:15328-15331
Publication Date(Web):20 Aug 2015
DOI:10.1039/C5CC06428G
A Rh(III)-catalyzed cross-coupling/cyclization cascade of α-imino Csp3–H bonds with donor/acceptor α-acyl diazocarbonyl compounds has been developed. This novel transformation involves ligand-directed Csp3–H bond functionalization with carbenoids under the pyridine-chelation assistance, and offered an efficient access to synthetically versatile polysubstituted N-(2-pyridyl)pyrroles with a broad range of functional group tolerance.
Co-reporter:Ying Xie, Tengfei Chen, Shaomin Fu, Huanfeng Jiang and Wei Zeng
Chemical Communications 2015 vol. 51(Issue 45) pp:9377-9380
Publication Date(Web):27 Apr 2015
DOI:10.1039/C5CC02631H
The Pd(II)-catalyzed pyridine-directed carbonylative cycloamidation of ketoimines has provided an efficient protocol for assembly of pyrido[1,2-a]pyrimidin-4-ones.
Co-reporter:Jianzhong Liu, Ying Xie, Wei Zeng, Dongen Lin, Yuanfu Deng, and Xiaoxia Lu
The Journal of Organic Chemistry 2015 Volume 80(Issue 9) pp:4618-4626
Publication Date(Web):April 7, 2015
DOI:10.1021/acs.joc.5b00489
A novel Pd(II)-catalyzed pyridine N-oxide directed remote arylation of unactivated Csp3–H bonds in aliphatic amides with aryl iodides has been developed. This protocol allows installing various aryl groups at the β- or γ-Csp3 atom of alkyl carboxylic acid amides. The key palladabicyclic intermediate of this transformation has been identified by HR-MS and 1H NMR method.
Co-reporter:Ying Xie, Tengfei Chen, Shaomin Fu, Xing-Shu Li, Yuanfu Deng, Huanfeng Jiang and Wei Zeng
Chemical Communications 2014 vol. 50(Issue 73) pp:10699-10702
Publication Date(Web):24 Jul 2014
DOI:10.1039/C4CC04676E
The Pd(II)-catalyzed oxidative [3+2] cycloaddition of N-(2-pyridyl) ketoimines with internal alkynes has been developed. The transformation is tolerant of extensive substitution on halogen, alkene, alkyne, hydroxyl, aryl and acyl groups, and allows facile assembly of multisubstituted pyrroles.
Co-reporter:Mingyang Li, Ying Xie, Yong Ye, Yong Zou, Huanfeng Jiang, and Wei Zeng
Organic Letters 2014 Volume 16(Issue 23) pp:6232-6235
Publication Date(Web):November 21, 2014
DOI:10.1021/ol503165b
A copper(I)-catalyzed direct transannulation of N-heteroaryl aldehydes or ketones with alkylamines via Csp3–H amination has been achieved using molecular oxygen as a sole oxidant. N-Heteroarenes are employed as the amine source. This transformation provides a rapid and concise access to multifunctional imidazo[1,5-a]pyridines.
Co-reporter:Cheng Qian, Dongen Lin, Yuanfu Deng, Xiao-Qi Zhang, Huanfeng Jiang, Guang Miao, Xihao Tang and Wei Zeng
Organic & Biomolecular Chemistry 2014 vol. 12(Issue 31) pp:5866-5875
Publication Date(Web):11 Jun 2014
DOI:10.1039/C4OB00993B
With the aid of an azo directing group, Pd-catalyzed ortho-sp2 C–H bond activation/functionalization of azoarenes with aryl acyl peroxides has been explored. This transformation provides easy access to regioselectively introducing acyloxyl and aryl groups into azoarenes by simply changing the reaction temperature and solvent.
Co-reporter:Meiqin Fu, Dongen Lin, Yuanfu Deng, Xiao-Qi Zhang, Yanchu Liu, Chunsong Lai and Wei Zeng
RSC Advances 2014 vol. 4(Issue 45) pp:23595-23603
Publication Date(Web):20 May 2014
DOI:10.1039/C4RA02055C
A Pd-catalyzed cascade Ullmann coupling–aldol–dehydration reaction of ortho-acylphenyl iodides has been explored. This transformation provides a concise access to colchino analogues in moderate to good yields with wide functional group tolerance.
Co-reporter:Libo Liang, Shaomin Fu, Dongen Lin, Xiao-Qi Zhang, Yuanfu Deng, Huanfeng Jiang, and Wei Zeng
The Journal of Organic Chemistry 2014 Volume 79(Issue 20) pp:9472-9480
Publication Date(Web):September 24, 2014
DOI:10.1021/jo501460h
A ruthenium-catalyzed C2-hydroindolation of alkynes has been achieved. This protocol provides a rapid and concise access to kinds of 2-alkenyl-substituted N-(2-pyridyl)indoles in which the pyridyl moiety can be easily removed to afford free (N–H) indoles under mild conditions. Various arenes and alkynes, including electron-deficient and electron-rich internal alkynes and terminal alkynes, allow for this transformation.
Co-reporter:Ling Dang, Libo Liang, Cheng Qian, Meiqin Fu, Tongmei Ma, Dingguo Xu, Huanfeng Jiang, and Wei Zeng
The Journal of Organic Chemistry 2014 Volume 79(Issue 2) pp:769-776
Publication Date(Web):December 31, 2013
DOI:10.1021/jo402705w
A Cu(OAc)2-promoted cascade carboamination/oxidative cyclization of alkenes with α-imino esters has been explored. This transformation provides a concise approach to rapid assembly of 2-oxo-3-iminopyrrole derivatives in moderate to good yields.
Co-reporter:Feng Xiong, Cheng Qian, Dongen Lin, Wei Zeng, and Xiaoxia Lu
Organic Letters 2013 Volume 15(Issue 21) pp:5444-5447
Publication Date(Web):October 11, 2013
DOI:10.1021/ol402537t
A Pd-catalyzed cascade oxidation/sp2 C–H bond acylation of azoarenes was developed in which readily available aryl methanes were used as the in situ generated acyl sources. This reaction provides a convenient access to ortho-acyl azoarenes under mild conditions.
Co-reporter:Shujie Zhu, Xiaoxia Lu, Yueting Luo, Wei Zhang, Huanfeng Jiang, Ming Yan, and Wei Zeng
Organic Letters 2013 Volume 15(Issue 7) pp:1440-1443
Publication Date(Web):March 15, 2013
DOI:10.1021/ol4006079
A method for the highly regioselective reductive coupling reaction of N-aryl-α-imino esters with dienes is described. The method utilizes the RuHCl(CO)(PPh3)3/iPrOH catalytic system under an Ar atmosphere and provides α-branched allylic α-amino acid derivatives. Application of this transformation to the concise synthesis of a natural plant growth regulator is demonstrated.
Co-reporter:Cheng Qian, Jiayan Chen, Meiqin Fu, Shiya Zhu, Wen-Hua Chen, Huanfeng Jiang and Wei Zeng
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 36) pp:6013-6022
Publication Date(Web):16 Jul 2013
DOI:10.1039/C3OB41011K
The Pd-catalyzed cross-coupling ethoxycarbonylation of aryl boronic acids with N-aryl-α-iminoesters affords aryl carboxylic esters via carbonyl-imino σ bond cleavage. This unprecedented mode of reaction allows regioselective installation of the ethoxycarbonyl group into target molecules. Mechanism studies have revealed that an unusual 1,2-aryl shift process is involved in the transformation.
Co-reporter:Yueting Luo, Xiaoxia Lu, Yong Ye, Ya Guo, Huanfeng Jiang, and Wei Zeng
Organic Letters 2012 Volume 14(Issue 22) pp:5640-5643
Publication Date(Web):October 26, 2012
DOI:10.1021/ol302483f
A novel cascade cyclization of ethyl glyoxalate and amines proceeds in the presence of Pd(TFA)2 (5 mol %) to give the cyclic dehydro-α-amino acid derivatives. This method provides a fast and simple access to highly substituted dihydro-pyrrol-2-ones in good yields.
Co-reporter:Jiayan Chen, Xiaoxia Lu, Wenyong Lou, Yong Ye, Huanfeng Jiang, and Wei Zeng
The Journal of Organic Chemistry 2012 Volume 77(Issue 19) pp:8541-8548
Publication Date(Web):September 18, 2012
DOI:10.1021/jo301423e
A protocol for Pd(II)-catalyzed asymmetric arylation of N-aryl imino esters has been developed. The method affords a practical and direct access to chiral arylglycine derivatives in good yields and with high enantioselectivities.
Co-reporter:Shujie Zhu, Jia Dong, Shaomin Fu, Huanfeng Jiang, and Wei Zeng
Organic Letters 2011 Volume 13(Issue 18) pp:4914-4917
Publication Date(Web):August 23, 2011
DOI:10.1021/ol2019955
C-Acylimines 1 undergo intermolecular amidation with amides 2 to produce monoacyl gem-diamino acid derivatives 3 upon treatment with Cu(OTf)2 (20 mol %)/ PPh3 (20 mol %) under mild conditions. This method provides an efficient access to gem-diamino acid equivalents with good to excellent yields.
Co-reporter:Shaomin Fu;Huanfeng Jiang;Yuanfu Deng
Advanced Synthesis & Catalysis 2011 Volume 353( Issue 14-15) pp:2795-2804
Publication Date(Web):
DOI:10.1002/adsc.201100370
Abstract
O-Sulfonamidophenylimines undergo intramolecular sulfonamidation/oxidation to produce 1,2-disubstituted benzimidazoles upon treatment with palladium(II) chloride/(diacetoxyiodo)benzene and potassium carbonate at room temperature. The substituent scope at the 2-position of the benzimidazole can be extended to alkyl, aryl, alkenyl, acyl, and ester functional groups under mild conditions.
Co-reporter:Xiaoyan Lian;Shaomin Fu;Tongmei Ma;Shunbin Li
Applied Organometallic Chemistry 2011 Volume 25( Issue 6) pp:443-447
Publication Date(Web):
DOI:10.1002/aoc.1784
Abstract
A reliable and practical procedure for FeCl3-promoted ester cleavage has been developed. Lewis acids including TiCl4, ZnO and FeCl3 etc. were investigated as promoters for O-alkyl cleavage of carboxylic acid ester. Under optimal reaction conditions, FeCl3 (1.5 equiv.) was found to possess the highest activity and efficiently enhanced dealkylation of aryl esters, alkyl esters and aromatic heterocyclic esters to give their corresponding carboxylic acids in 54–98% yield, the method provides a complementary access to dealkylation of ester under neutral condition. Copyright © 2011 John Wiley & Sons, Ltd.
Co-reporter:Shaomin Fu, Xiaoyan Lian, Tongmei Ma, Wenhua Chen, Meifang Zheng, Wei Zeng
Tetrahedron Letters 2010 Volume 51(Issue 44) pp:5834-5837
Publication Date(Web):3 November 2010
DOI:10.1016/j.tetlet.2010.08.092
Several Lewis acids were investigated as promoters in the intermolecular or intramolecular direct N-acylation reaction of sulfonamides using carboxylic ester as an acylating agent. TiCl4 was found to possess the highest activity and enhanced efficiently sulfonamide to form N-acylsulfonamides under optimized conditions. This method provides a novel approach to make N-acylsulfonamides from ester via an easy work-up procedure.Several Lewis acids were investigated as promoters in the intermolecular or intramolecular direct N-acylation reaction of sulfonamides using carboxylic ester as an acylating agent. TiCl4 was found to possess the highest activity and enhanced efficiently sulfonamide to form N-acylsulfonamides under optimized conditions. This method provides a novel approach to make N-acylsulfonamides from ester via an easy work-up procedure.
Co-reporter:Xinsheng Xiao; Ying Xie; Siyi Bai; Yuanfu Deng; Huanfeng Jiang
Organic Letters () pp:
Publication Date(Web):July 31, 2015
DOI:10.1021/acs.orglett.5b01868
An efficient one-pot and transition-metal-free chlorocyclization cascade of 2-aminopyridines with aliphatic carboxylic acids is reported. This transformation provides a novel approach to 2-chloro- or 3-chloro-substituted imidazo[1, 2-α]pyridines with a broad range of substrate scopes.
Co-reporter:Ying Xie, Xun Chen, Xin Liu, Shi-Jian Su, Jianzhang Li and Wei Zeng
Chemical Communications 2016 - vol. 52(Issue 34) pp:NaN5859-5859
Publication Date(Web):2016/03/29
DOI:10.1039/C6CC00254D
A novel Rh(III)-catalyzed relay cross-coupling/cyclization cascade between arylketoimines and diazoesters is described. This transformation provides a concise access to unique π-conjugated 1-azaphenalenes (1-APLEs) via a double aryl Csp2–H bond carbenoid functionalization process. As illustrative examples, the 1-APLE-based π-conjugated molecules which possess low-lying HOMO levels could be converted to promising organic optoelectronic materials.
Co-reporter:Ying Xie, Tengfei Chen, Shaomin Fu, Huanfeng Jiang and Wei Zeng
Chemical Communications 2015 - vol. 51(Issue 45) pp:NaN9380-9380
Publication Date(Web):2015/04/27
DOI:10.1039/C5CC02631H
The Pd(II)-catalyzed pyridine-directed carbonylative cycloamidation of ketoimines has provided an efficient protocol for assembly of pyrido[1,2-a]pyrimidin-4-ones.
Co-reporter:Xun Chen, Ying Xie, Xinsheng Xiao, Guoqiang Li, Yuanfu Deng, Huanfeng Jiang and Wei Zeng
Chemical Communications 2015 - vol. 51(Issue 83) pp:NaN15331-15331
Publication Date(Web):2015/08/20
DOI:10.1039/C5CC06428G
A Rh(III)-catalyzed cross-coupling/cyclization cascade of α-imino Csp3–H bonds with donor/acceptor α-acyl diazocarbonyl compounds has been developed. This novel transformation involves ligand-directed Csp3–H bond functionalization with carbenoids under the pyridine-chelation assistance, and offered an efficient access to synthetically versatile polysubstituted N-(2-pyridyl)pyrroles with a broad range of functional group tolerance.
Co-reporter:Cheng Qian, Jiayan Chen, Meiqin Fu, Shiya Zhu, Wen-Hua Chen, Huanfeng Jiang and Wei Zeng
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 36) pp:NaN6022-6022
Publication Date(Web):2013/07/16
DOI:10.1039/C3OB41011K
The Pd-catalyzed cross-coupling ethoxycarbonylation of aryl boronic acids with N-aryl-α-iminoesters affords aryl carboxylic esters via carbonyl-imino σ bond cleavage. This unprecedented mode of reaction allows regioselective installation of the ethoxycarbonyl group into target molecules. Mechanism studies have revealed that an unusual 1,2-aryl shift process is involved in the transformation.
Co-reporter:Ying Xie, Tengfei Chen, Shaomin Fu, Xing-Shu Li, Yuanfu Deng, Huanfeng Jiang and Wei Zeng
Chemical Communications 2014 - vol. 50(Issue 73) pp:NaN10702-10702
Publication Date(Web):2014/07/24
DOI:10.1039/C4CC04676E
The Pd(II)-catalyzed oxidative [3+2] cycloaddition of N-(2-pyridyl) ketoimines with internal alkynes has been developed. The transformation is tolerant of extensive substitution on halogen, alkene, alkyne, hydroxyl, aryl and acyl groups, and allows facile assembly of multisubstituted pyrroles.
Co-reporter:Cheng Qian, Dongen Lin, Yuanfu Deng, Xiao-Qi Zhang, Huanfeng Jiang, Guang Miao, Xihao Tang and Wei Zeng
Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 31) pp:NaN5875-5875
Publication Date(Web):2014/06/11
DOI:10.1039/C4OB00993B
With the aid of an azo directing group, Pd-catalyzed ortho-sp2 C–H bond activation/functionalization of azoarenes with aryl acyl peroxides has been explored. This transformation provides easy access to regioselectively introducing acyloxyl and aryl groups into azoarenes by simply changing the reaction temperature and solvent.
Co-reporter:Siyi Bai, Xun Chen, Xinwei Hu, Yuanfu Deng, Huanfeng Jiang and Wei Zeng
Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 17) pp:NaN3647-3647
Publication Date(Web):2017/04/03
DOI:10.1039/C7OB00367F
An Ir(III)-catalyzed relay aryl C–H bond carbenoid insertion cascade of N-aryl-2-pyridinamines with diazo Meldrum's acid has been developed. This method provides an efficient approach to multifunctionalized 1,3-dihydroindol-2-ones with a broad range of functional group tolerance. Furthermore, this protocol could be applied for the concise synthesis of bioactive hematopoietic growth factor analogues.