Cascade Synthesis of 3-Alkylidene Dihydrobenzofuran Derivatives via Rhodium(III)-Catalyzed Redox-Neutral C-H Functionalization/Cyclization

被引：68

作者：

Zhou, Zhi ^{[1
]}

Liu, Guixia ^{[1
]}

Chen, Yan ^{[1
]}

Lu, Xiyan ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 23期

基金：

中国国家自然科学基金;

关键词：

N-PHENOXYACETAMIDES; INDOLE SYNTHESIS; ACTIVATION; BOND; ALKYNES; MILD; ANNULATION; ACCESS; ARYLNITRONES; CONSTRUCTION;

D O I：

10.1021/acs.orglett.5b03060

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient rhodium(III)-catalyzed coupling reaction of N-phenoxyacetamides with propargyl carbonates to yield 3-alkylidene dihydrobenzofuran derivatives via C-H functionalization/cascade cyclization has been developed. This transformation represents a redox-neutral process and features the formation of three new bonds under mild conditions.

引用

收藏

页码：5874 / 5877

页数：4

相关论文

共 55 条

[1] A multitasking functional group leads to structural diversity using designer C-H activation reaction cascades [J].

Chen, Ying ;

Wang, Dongqi ;

Duan, Pingping ;

Ben, Rong ;

Dai, Lu ;

Shao, Xiaoru ;

Hong, Mei ;

Zhao, Jing ;

Huang, Yong .

NATURE COMMUNICATIONS, 2014, 5

[2] Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions [J].

Colby, Denise A. ;

Tsai, Andy S. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825

[3] Selective Cyclization of Arylnitrones to Indolines under External Oxidant-Free Conditions: Dual Role of Rh(III) Catalyst in the C-H Activation and Oxygen Atom Transfer [J].

Dateer, Ramesh B. ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (15) :4908-4911

[4] Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon-Hydrogen Bonds [J].

Daugulis, Olafs ;

Roane, James ;

Tran, Ly Dieu .

ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (04) :1053-1064

[5] RhIII-Catalyzed Redox-Neutral C-H Activation of Pyrazolones: An Economical Approach for the Synthesis of N-Substituted Indoles [J].

Fan, Zhoulong ;

Song, Shanshan ;

Li, Wei ;

Geng, Kaijun ;

Xu, Youjun ;

Miao, Ze-Hong ;

Zhang, Ao .

ORGANIC LETTERS, 2015, 17 (02) :310-313

[6] Low-Valent Cobalt Catalysis: New Opportunities for C-H Functionalization [J].

Gao, Ke ;

Yoshikai, Naohiko .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (04) :1208-1219

[7] The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations [J].

Girard, Simon A. ;

Knauber, Thomas ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :74-100

[8] Rhodium(III)-Catalyzed Heterocycle Synthesis Using an Internal Oxidant: Improved Reactivity and Mechanistic Studies [J].

Guimond, Nicolas ;

Gorelsky, Serge I. ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (16) :6449-6457

[9] Rhodium(III)-Catalyzed Isoquinolone Synthesis: The N-O Bond as a Handle for C-N Bond Formation and Catalyst Turnover [J].

Guimond, Nicolas ;

Gouliaras, Christina ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (20) :6908-+

[10] Rhodium(III)-Catalyzed ortho Alkenylation of N-Phenoxyacetamides with N-Tosylhydrazones or Diazoesters through C-H Activation [J].

Hu, Fangdong ;

Xia, Ying ;

Ye, Fei ;

Liu, Zhenxing ;

Ma, Chen ;

Zhang, Yan ;

Wang, Jianbo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (05) :1364-1367

← 1 2 3 4 5 6 →