Yanzhong Li

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Name: 李艳忠; Li, YanZhong
Organization: East China Normal University , China
Department: Department of Chemistry
Title: Professor(PhD)

TOPICS

Co-reporter:Yulei Zhao, Yang Yuan, Xiaoyu Wang, and Yanzhong Li
The Journal of Organic Chemistry October 20, 2017 Volume 82(Issue 20) pp:11198-11198
Publication Date(Web):October 2, 2017
DOI:10.1021/acs.joc.7b01614
A novel methodology for stereoselective synthesis of benzo[b]indolo[3,2,1-de]acridines through the tandem reaction of propargylic compounds with organoboron is described, and only one diastereoisomer was obtained. The sequential procedure was triggered by Pd(0)-catalyzed allenylation of propargyl carbonate. Then, Diels–Alder cyclization and hydrogen migration processes proceeded successively to furnish the polycyclic target molecules. Control reactions suggested the base (Cs2CO3) was indispensable for the hydrogen migration.
Co-reporter:Qiyi Yao;Lingkai Kong;Fangfang Zhang;Xianghua Tao
Advanced Synthesis & Catalysis 2017 Volume 359(Issue 18) pp:3079-3084
Publication Date(Web):2017/09/18
DOI:10.1002/adsc.201700565
AbstractBase-promoted insertion reactions of alkynes into the C–C σ-bonds of α-cyano ketones were established to construct highly functionalized conjugated olefins or chromone derivatives via transition metal-free tandem reactions. These reactions are initialized through the nucleophilic attack of α-cyano ketones to alkynones followed by intramolecular nucleophilic addition/ring-opening to furnish the cyano-containing alkenes. In the cases of alkynones bearing an ortho-halide-substituted aryl ring, a further C–O bond coupling reaction occurs to afford chromone derivatives in good to high yields. Various alkynones bearing alkyl or aryl substituents were compatible in the reaction. This reaction has the potential to become a general synthetic protocol for the preparation of cyano-substituted olefins and chromones due to the abundance of easily accessible starting materials possessing diverse substituent groups.
Co-reporter:Fangfang Zhang;Qiyi Yao;Yang Yuan;Murong Xu;Lingkai Kong
Organic & Biomolecular Chemistry 2017 vol. 15(Issue 12) pp:2497-2500
Publication Date(Web):2017/03/22
DOI:10.1039/C7OB00476A
Transition-metal free insertions of alkynes into carbon–carbon σ-bonds of ethanones have been reported. These tandem reactions offer an efficient synthesis of hydroxydienones and multi-substituted chromones. This is the first example of base-promoted insertion reactions of isolated carbon–carbon triple bonds into carbon–carbon σ-bonds with active methylene compounds bearing only one electron-withdrawing group.
Co-reporter:Yulei Zhao;Murong Xu;Zhong Zheng;Yang Yuan
Chemical Communications 2017 vol. 53(Issue 26) pp:3721-3724
Publication Date(Web):2017/03/28
DOI:10.1039/C7CC00005G
A novel methodology for the synthesis of 3-alkenyl indolines through the reaction of in situ generated allenes with N-benzylic Csp3–H has been developed. The reaction was realized by Pd(0) catalyzed allenylation of propargyl carbonate with organoboron and subsequent tertiary amine self-catalyzed Csp3–H functionalization in a one-pot process. Control reactions suggested that the substrate itself might also serve as a Lewis base for the N-benzylic Csp3–H functionalization.
Co-reporter:Yulei Zhao;Yang Yuan;Murong Xu;Zhong Zheng;Runhua Zhang
Organic & Biomolecular Chemistry 2017 vol. 15(Issue 30) pp:6328-6332
Publication Date(Web):2017/08/02
DOI:10.1039/C7OB01516J
Novel methodologies for the selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles starting from pyrrole derivatives and alkynones are described. When reactions were carried out with 1,2,4-trisubstituted N-propargyl pyrroles using a ZnI2 catalyst, pyrrolo[1,2-a]azepines were obtained. Whereas 4,6-dicarbonyl indoles were produced selectively with 1,2-disubstituted pyrroles in the presence of silica gel. The reaction outcomes depend on the substituent pattern of the substrates and the nature of the catalysts chosen. Control reactions suggested that the formation of a conjugated enamine intermediate was crucial for both the processes. With easily accessible starting materials, inexpensive catalysts and an easy-to-handle procedure, this reaction has the potential to become a general protocol for the synthesis of pyrrolo[1,2-a]azepines or indoles.
Co-reporter:Fangfang Zhang, Zhengchen Qin, Lingkai Kong, Yulei Zhao, Yuanyuan Liu, and Yanzhong Li
Organic Letters 2016 Volume 18(Issue 19) pp:5150-5153
Publication Date(Web):September 21, 2016
DOI:10.1021/acs.orglett.6b02615
Synthetic methods involving chemoselective tandem reactions for the synthesis of α-naphthylamines and indeno[1,2-c]pyrrolones starting from (o-aklynyl)phenyl enaminones are described. When reactions were carried out in N,N-dimethylformamide (DMF) using a AgNO3 catalyst, α-naphthylamines were obtained in up to 89% isolated yields within 2 h. Whereas indeno[1,2-c]pyrrolones were produced in high isolated yields in the presence of benzoyl peroxide (BPO) and CuCl catalysis.
Co-reporter:Lingkai Kong, Mengdan Wang, Fangfang Zhang, Murong Xu, and Yanzhong Li
Organic Letters 2016 Volume 18(Issue 23) pp:6124-6127
Publication Date(Web):November 14, 2016
DOI:10.1021/acs.orglett.6b03131
A copper-catalyzed oxidative dearomatization/spirocyclization of indole-2-carboxamides using tert-butyl hydroperoxide (TBHP) as the oxidant has been developed that provides rapid and efficient access to C2-spiro-pseudoindoxyls. Two of the sp2 C–H bonds are functionalized during the reaction process, and the reaction likely proceeds via the formation of a highly reactive 3H-indol-3-one intermediate followed by aromatic electrophilic substitution with the N-aryl ring of the amide moiety.
Co-reporter:Yulei Zhao, Qizhao Duan, Yuanyuan Zhou, Qiyi Yao and Yanzhong Li  
Organic & Biomolecular Chemistry 2016 vol. 14(Issue 7) pp:2177-2181
Publication Date(Web):12 Jan 2016
DOI:10.1039/C5OB02556G
An efficient tandem Au(I)/TsOH-catalyzed reaction of enaminones with diazo compounds for the synthesis of pyrroloquinolinone derivatives under mild reaction conditions has been developed. This methodology was realized by relay actions of Au and TsOH in a one-pot multistep manner. Initially, the Au-catalyzed reaction of enaminones with diazo compounds affords chemo- and diastereoselective C(sp2)–H functionalized products, which then undergo subsequent intramolecular cyclization/rearrangement to give pyrroloquinolinone derivatives under the catalysis of TsOH.
Co-reporter:Xingcan Cheng;Yuanyuan Zhou;Fangfang Zhang;Kai Zhu;Dr. Yuanyuan Liu ;Dr. Yanzhong Li
Chemistry - A European Journal 2016 Volume 22( Issue 36) pp:12655-12659
Publication Date(Web):
DOI:10.1002/chem.201602064

Abstract

Tandem reactions using base-promoted processes have been developed for the synthesis of xanthone and chromone derivatives. The first examples of base-promoted insertion reactions of isolated carbon–carbon triple bonds into carbon–carbon σ-bonds have been reported. Using these approaches, polycyclic structures can be prepared. This reaction has the potential to become a general synthetic protocol for the preparation of multi-substituted xanthones and chromones due to the abundance of easily accessible starting materials possessing diverse substituent groups.

Co-reporter:Lingkai Kong, Yuanyuan Zhou, He Huang, Yang Yang, Yuanyuan Liu, and Yanzhong Li
The Journal of Organic Chemistry 2015 Volume 80(Issue 2) pp:1275-1278
Publication Date(Web):December 15, 2014
DOI:10.1021/jo502630t
An efficient cascade copper-catalyzed intermolecular Ullmann-type C–N coupling/enamine condensation reaction is described, in which ortho-acylanilines and alkenyl iodides converted to multisubstituted quinolines in good to excellent yields.
Co-reporter:Lingkai Kong, Yushang Shao, Yanli Li, Yuanyuan Liu, and Yanzhong Li
The Journal of Organic Chemistry 2015 Volume 80(Issue 24) pp:12641-12645
Publication Date(Web):November 18, 2015
DOI:10.1021/acs.joc.5b02211
An efficient cascade β-metalation/addition/cyclization reaction promoted by LDA is described in which 3-amino furans were constructed from enaminones and aldehydes. A broad range of substituents on the starting compounds was tolerated, and the polysubstituted furans were gained with moderate to excellent yields within 2 h.
Co-reporter:Chengyu Wang, Chunyi Dong, Lingkai Kong, Yanli Li and Yanzhong Li  
Chemical Communications 2014 vol. 50(Issue 17) pp:2164-2166
Publication Date(Web):03 Jan 2014
DOI:10.1039/C3CC49191A
A highly efficient ZnCl2-catalyzed cascade reaction of enaminones with 2-furylcarbinols under mild reaction conditions has been developed. This methodology offers a chemo- and diastereo-selective access to functionalized cyclopenta[b]pyrrole derivatives in good to excellent yields.
Co-reporter:Chengyu Wang;Lingkai Kong;Yanli Li
European Journal of Organic Chemistry 2014 Volume 2014( Issue 17) pp:3556-3560
Publication Date(Web):
DOI:10.1002/ejoc.201402059

Abstract

A highly efficient palladium-catalyzed cascade reaction of propargyl carboxylates bearing a furanyl group with organoborons was developed. This methodology offers rapid access to polycyclic Diels–Alder cycloadducts in good to high yields. The thus-formed oxygen-bridged products were further converted into anthracene derivatives in a chemoselective manner under mild conditions.

Co-reporter:Ende Li, Xingcan Cheng, Chengyu Wang, Xia Sun and Yanzhong Li  
RSC Advances 2013 vol. 3(Issue 45) pp:22872-22876
Publication Date(Web):01 Oct 2013
DOI:10.1039/C3RA44595J
A highly efficient copper-catalyzed cascade reaction of aryloxy-enynes with amines under mild reaction conditions has been developed. This methodology offers rapid access to 1,2,4-trisubstituted pyrroles in good to excellent yields in a regioselective manner.
Co-reporter:Yushang Shao, Kai Zhu, Zhengchen Qin, Ende Li, and Yanzhong Li
The Journal of Organic Chemistry 2013 Volume 78(Issue 11) pp:5731-5736
Publication Date(Web):May 7, 2013
DOI:10.1021/jo4005553
A highly efficient BF3·Et2O-catalyzed cascade reaction of enaminones with propargylic alcohols under mild reaction conditions has been developed. This methodology offers regioselective access to multisubstituted 1,2-dihydropyridines in good to excellent yields.
Co-reporter:Ende Li, Wenjun Yao, Xin Xie, Chengyu Wang, Yushang Shao and Yanzhong Li  
Organic & Biomolecular Chemistry 2012 vol. 10(Issue 15) pp:2960-2965
Publication Date(Web):24 Feb 2012
DOI:10.1039/C2OB07173H
A series of (E)-1-aryloxy-1-en-3-ynes has been prepared by Sonogashira coupling of 2-bromo-3-aryloxypropenoates with terminal alkynes using Pd(PPh3)4 and CuI as the catalysts in Et3N. The resulting enynyl-aryl ethers are found to be highly applicable to the synthesis of 2,4-disubstituted furans with an ester group at C-4 position through an Au/Ag-catalyzed annulation reaction under extremely mild reaction conditions.
Co-reporter:Chengyu Wang, Jingyu Yang, Xingcan Cheng, Ende Li, Yanzhong Li
Tetrahedron Letters 2012 Volume 53(Issue 33) pp:4402-4404
Publication Date(Web):15 August 2012
DOI:10.1016/j.tetlet.2012.06.030
An efficient I2-mediated approach to the synthesis of disubstituted indenones from readily available 2-alkynylbenzyl alcohols in the presence of H2O has been developed. These results are different from the known iodocyclization reactions in which O-containing heterocycles are obtained.
Co-reporter:JingYu Yang;ChunYi Dong;HaiYan Li;HongFeng Li
Science Bulletin 2012 Volume 57( Issue 19) pp:2364-2367
Publication Date(Web):2012 July
DOI:10.1007/s11434-012-5144-9
An efficient one-pot procedure for the synthesis of multisubstituted xanthone derivatives using Fe-catalyzed reactions of 2-aryloxybenzaldehydes followed by DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) oxidation has been developed. This method offers a convenient high-yield route to xanthones from easily accessible starting materials.
Co-reporter:Ende Li, Xingcan Cheng, Chengyu Wang, Yushang Shao, and Yanzhong Li
The Journal of Organic Chemistry 2012 Volume 77(Issue 17) pp:7744-7748
Publication Date(Web):August 13, 2012
DOI:10.1021/jo3012545
A highly efficient palladium-catalyzed cascade reactions of aryloxy-enynes with aryl halides under mild reaction conditions has been developed. This methodology offers rapid access to 2,3,4-trisubstituted furans in good to excellent yields in a regioselective manner.
Co-reporter:Jingyu Yang, Chengyu Wang, Xin Xie, Hongfeng Li, Ende Li and Yanzhong Li  
Organic & Biomolecular Chemistry 2011 vol. 9(Issue 5) pp:1342-1346
Publication Date(Web):20 Dec 2010
DOI:10.1039/C0OB00985G
An efficient palladium/copper-catalyzed approach to the synthesis of highly substituted 3-formyl furans from the reactions of readily available α-bromoenaminones with terminal alkynes has been developed. This methodology was realized by the cascade reactions of Sonogashira coupling and the subsequent intramolecular cyclization.
Co-reporter:Hongfeng Li, Chengyu Wang, He Huang, Xiaolei Xu, Yanzhong Li
Tetrahedron Letters 2011 Volume 52(Issue 10) pp:1108-1111
Publication Date(Web):9 March 2011
DOI:10.1016/j.tetlet.2010.12.102
An efficient silver-catalyzed, aniline mediated cascade hydroamination/cycloaddition of o-aminoaryl compounds including o-aminoaryl aldehydes, o-aminoaryl ketones with alkynes for the synthesis of 2- or 2,4-substituted quinolines is reported. The reactions proceed with high regioselectivity to afford mono- or disubstituted quinoline derivatives in good to high yields using AgOTf as the catalyst in the air.
Co-reporter:Hongfeng Li, Xiaolei Xu, Jingyu Yang, Xin Xie, He Huang, Yanzhong Li
Tetrahedron Letters 2011 Volume 52(Issue 4) pp:530-533
Publication Date(Web):26 January 2011
DOI:10.1016/j.tetlet.2010.11.106
An efficient iron-catalyzed cascade Michael addition–cyclization of o-aminoaryl compounds including o-aminoaryl aldehydes, o-aminoaryl ketones, and o-aminobenzyl alcohols with ynones for the synthesis of 3-carbonyl quinolines is reported. The reactions proceed to afford 3-carbonyl quinoline derivatives with or without substituent at the C-4 position in good to high yields using Iron(III) chloride hexahydrate as the catalyst in the air.
Co-reporter:Xiaobing Xu, Xiaolei Xu, Hongfeng Li, Xin Xie and Yanzhong Li
Organic Letters 2010 Volume 12(Issue 1) pp:100-103
Publication Date(Web):November 25, 2009
DOI:10.1021/ol902489a
An efficient iron-catalyzed, microwave-promoted cascade benzylation−cyclization of phenols is reported. Benzyl acetates, benzyl bromides, and benzyl carbonates are suitable benzylating reagents. The reactions proceed to afford both 9-aryl and 9-alkyl xanthene derivatives in good to high yields using FeCl3 as the catalyst under MW irradiation conditions.
Co-reporter:Jingyu Yang;Chengyu Wang;Xin Xie;Hongfeng Li
European Journal of Organic Chemistry 2010 Volume 2010( Issue 22) pp:4189-4193
Publication Date(Web):
DOI:10.1002/ejoc.201000607

Abstract

An efficient acid-catalyzed approach to the synthesis of functional 1,4-dihydropyridines from the reaction of readily available enaminones with aldehydes has been developed. This methodology was realized by a cascade reaction involving first formation of divinylmethanes and subsequent intramolecular cyclization.

Co-reporter:Xin Xie;Xiaobing Xu;Hongfeng Li;Xiaolei Xu;Jingyu Yang
Advanced Synthesis & Catalysis 2009 Volume 351( Issue 9) pp:1263-1267
Publication Date(Web):
DOI:10.1002/adsc.200900123
Co-reporter:Xiaobing Xu;Jun Liu;Linfeng Liang;Hongfeng Li
Advanced Synthesis & Catalysis 2009 Volume 351( Issue 16) pp:2599-2604
Publication Date(Web):
DOI:10.1002/adsc.200900483

Abstract

An efficient, regioselective, iron-catalyzed intramolecular hydroaryloxylation of 2-propargylphenols or naphthols is reported. The reactions proceed through an endo-dig cyclization to afford benzopyran or naphthopyran derivatives in good to high yields using iron(III) chloride as the catalyst with the assistance of aniline in dimethylformamide (DMF).

Co-reporter:Xiaobing Xu, Linfeng Liang, Jun Liu, Jingyu Yang, Lugen Mai, Yanzhong Li
Tetrahedron Letters 2009 50(1) pp: 57-59
Publication Date(Web):
DOI:10.1016/j.tetlet.2008.10.080
Co-reporter:Hongfeng Li, Jun Liu, Bin Yan, Yanzhong Li
Tetrahedron Letters 2009 50(20) pp: 2353-2357
Publication Date(Web):
DOI:10.1016/j.tetlet.2009.02.204
Co-reporter:Ende Li, Xiaobing Xu, Hongfeng Li, Huimin Zhang, Xiaolei Xu, Xiyuan Yuan, Yanzhong Li
Tetrahedron 2009 65(44) pp: 8961-8968
Publication Date(Web):
DOI:10.1016/j.tet.2009.08.075
Co-reporter:Yulei Zhao, Qizhao Duan, Yuanyuan Zhou, Qiyi Yao and Yanzhong Li
Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 7) pp:NaN2181-2181
Publication Date(Web):2016/01/12
DOI:10.1039/C5OB02556G
An efficient tandem Au(I)/TsOH-catalyzed reaction of enaminones with diazo compounds for the synthesis of pyrroloquinolinone derivatives under mild reaction conditions has been developed. This methodology was realized by relay actions of Au and TsOH in a one-pot multistep manner. Initially, the Au-catalyzed reaction of enaminones with diazo compounds affords chemo- and diastereoselective C(sp2)–H functionalized products, which then undergo subsequent intramolecular cyclization/rearrangement to give pyrroloquinolinone derivatives under the catalysis of TsOH.
Co-reporter:Jingyu Yang, Chengyu Wang, Xin Xie, Hongfeng Li, Ende Li and Yanzhong Li
Organic & Biomolecular Chemistry 2011 - vol. 9(Issue 5) pp:NaN1346-1346
Publication Date(Web):2010/12/20
DOI:10.1039/C0OB00985G
An efficient palladium/copper-catalyzed approach to the synthesis of highly substituted 3-formyl furans from the reactions of readily available α-bromoenaminones with terminal alkynes has been developed. This methodology was realized by the cascade reactions of Sonogashira coupling and the subsequent intramolecular cyclization.
Co-reporter:Yulei Zhao, Murong Xu, Zhong Zheng, Yang Yuan and Yanzhong Li
Chemical Communications 2017 - vol. 53(Issue 26) pp:NaN3724-3724
Publication Date(Web):2017/03/09
DOI:10.1039/C7CC00005G
A novel methodology for the synthesis of 3-alkenyl indolines through the reaction of in situ generated allenes with N-benzylic Csp3–H has been developed. The reaction was realized by Pd(0) catalyzed allenylation of propargyl carbonate with organoboron and subsequent tertiary amine self-catalyzed Csp3–H functionalization in a one-pot process. Control reactions suggested that the substrate itself might also serve as a Lewis base for the N-benzylic Csp3–H functionalization.
Co-reporter:Ende Li, Wenjun Yao, Xin Xie, Chengyu Wang, Yushang Shao and Yanzhong Li
Organic & Biomolecular Chemistry 2012 - vol. 10(Issue 15) pp:NaN2965-2965
Publication Date(Web):2012/02/24
DOI:10.1039/C2OB07173H
A series of (E)-1-aryloxy-1-en-3-ynes has been prepared by Sonogashira coupling of 2-bromo-3-aryloxypropenoates with terminal alkynes using Pd(PPh3)4 and CuI as the catalysts in Et3N. The resulting enynyl-aryl ethers are found to be highly applicable to the synthesis of 2,4-disubstituted furans with an ester group at C-4 position through an Au/Ag-catalyzed annulation reaction under extremely mild reaction conditions.
Co-reporter:Chengyu Wang, Chunyi Dong, Lingkai Kong, Yanli Li and Yanzhong Li
Chemical Communications 2014 - vol. 50(Issue 17) pp:NaN2166-2166
Publication Date(Web):2014/01/03
DOI:10.1039/C3CC49191A
A highly efficient ZnCl2-catalyzed cascade reaction of enaminones with 2-furylcarbinols under mild reaction conditions has been developed. This methodology offers a chemo- and diastereo-selective access to functionalized cyclopenta[b]pyrrole derivatives in good to excellent yields.
Co-reporter:Fangfang Zhang, Qiyi Yao, Yang Yuan, Murong Xu, Lingkai Kong and Yanzhong Li
Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 12) pp:NaN2500-2500
Publication Date(Web):2017/03/07
DOI:10.1039/C7OB00476A
Transition-metal free insertions of alkynes into carbon–carbon σ-bonds of ethanones have been reported. These tandem reactions offer an efficient synthesis of hydroxydienones and multi-substituted chromones. This is the first example of base-promoted insertion reactions of isolated carbon–carbon triple bonds into carbon–carbon σ-bonds with active methylene compounds bearing only one electron-withdrawing group.
Co-reporter:Yulei Zhao, Yang Yuan, Murong Xu, Zhong Zheng, Runhua Zhang and Yanzhong Li
Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 30) pp:NaN6332-6332
Publication Date(Web):2017/07/13
DOI:10.1039/C7OB01516J
Novel methodologies for the selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles starting from pyrrole derivatives and alkynones are described. When reactions were carried out with 1,2,4-trisubstituted N-propargyl pyrroles using a ZnI2 catalyst, pyrrolo[1,2-a]azepines were obtained. Whereas 4,6-dicarbonyl indoles were produced selectively with 1,2-disubstituted pyrroles in the presence of silica gel. The reaction outcomes depend on the substituent pattern of the substrates and the nature of the catalysts chosen. Control reactions suggested that the formation of a conjugated enamine intermediate was crucial for both the processes. With easily accessible starting materials, inexpensive catalysts and an easy-to-handle procedure, this reaction has the potential to become a general protocol for the synthesis of pyrrolo[1,2-a]azepines or indoles.
5-fluoro-2-(2-phenylethynyl)benzaldehyde
Benzenemethanol, a-[(3,4,5-trimethoxyphenyl)ethynyl]-
Benzenemethanol, 2-chloro-a-(phenylethynyl)-
Benzenemethanol, a-ethynyl-2-(phenylethynyl)-
Benzaldehyde, 2-[(4-methoxyphenyl)ethynyl]-
Benzenemethanol, 4-bromo-α-(2-phenylethynyl)-
Benzenamine, 4-butyl-N-methyl-
Benzenemethanol, 2-bromo-α-(2-phenylethynyl)-
Benzenemethanol, a-[(4-methoxyphenyl)ethynyl]-
2-HEX-1-YNYL-BENZALDEHYDE