Rhodium-Catalyzed β-Selective Oxidative Heck-Type Coupling of Vinyl Acetate via C-H Activation

被引：34

作者：

Zhang, Hui-Jun ^{[1
]}

Lin, Weidong ^{[1
]}

Su, Feng ^{[1
]}

Wen, Ting-Bin ^{[1
]}

机构：

[1] Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Fujian, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 24期

关键词：

UNACTIVATED ALKENES; BOND ACTIVATION; BENZOIC-ACIDS; N-OXIDES; OLEFINATION; ARENES; ALKENYLATION; ARYLATION; ESTERS; FUNCTIONALIZATION;

D O I：

10.1021/acs.orglett.6b03244

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient Rh(III)-catalyzed direct ortho-C-H olefination of acetanilides with vinyl acetate was developed. This protocol provides a straightforward pathway to a series of (E)-2-acetamidostyryl acetates, giving access to indole derivatives following a simple hydrolysis/cyclization process.

引用

页码：6356 / 6359

页数：4

共 50 条

[21] Rhodium(III)-catalyzed internal oxidative coupling of N-hydroxyanilides with alkenes via C-H activation [J].

Wen, Jing ;

Wu, An ;

Chen, Pei ;

Zhu, Jin .

TETRAHEDRON LETTERS, 2015, 56 (38) :5282-5286

[22] Rhodium-catalyzed selective oxidative coupling of 7-azaindoles [J].

Li, Shuai-Shuai ;

Wang, Cheng-Qi ;

Li, Wei-Huan ;

Zhang, Xiao-Mei ;

Dong, Lin .

TETRAHEDRON, 2016, 72 (20) :2581-2586

[23] Rhodium-catalyzed hydroarylation of alkynes via tetrazole-directed C-H activation [J].

Chen, Bin ;

Jiang, Yan ;

Cheng, Jiang ;

Yu, Jin-Tao .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (10) :2901-2904

[24] Synthesis of Polyheteroaromatic Compounds via Rhodium-Catalyzed Multiple C-H Bond Activation and Oxidative Annulation [J].

Peng, Shiyong ;

Liu, Suna ;

Zhang, Sai ;

Cao, Shengyu ;

Sun, Jiangtao .

ORGANIC LETTERS, 2015, 17 (20) :5032-5035

[25] Grignard-Type Arylation of Aldehydes via a Rhodium-Catalyzed C-H Activation under Mild Conditions [J].

Yang, Luo ;

Correia, Camille A. ;

Li, Chao-Jun .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (08) :1269-1273

[26] Electrooxidative Rhodium-Catalyzed C-H/C-H Activation: Electricity as Oxidant for Cross-Dehydrogenative Alkenylation [J].

Qiu, Youai ;

Kong, Wei-Jun ;

Struwe, Julia ;

Sauermann, Nicolas ;

Rogge, Torben ;

Scheremetjew, Alexej ;

Ackermann, Lutz .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (20) :5828-5832

[27] Synthesis of Terminal Alkenylindolines via Rhodium-Catalyzed Direct C-H Alkenylation With Alkenyl Borates [J].

Wang, Liang ;

He, Xiaoyu ;

Luo, Cheng ;

Li, Pengjie ;

Mei, Yina ;

Gong, Cheng ;

Wang, Yimeng ;

Zhang, Jin .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2025, 62 (04) :362-368

[28] Rh(III)-Catalyzed Oxidative Coupling of Unactivated Alkenes via C-H Activation [J].

Tsai, Andy S. ;

Brasse, Mikael ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

ORGANIC LETTERS, 2011, 13 (03) :540-542

[29] Rhodium-Catalyzed Direct C-H Alkenylation of Indoles with Alkenyl Borates [J].

Wang, Ze-Tian ;

Zheng, Zi-Ang ;

Li, Peng-Jie ;

Zhou, Chun-Ni ;

Cai, Shao-Jun ;

Xiao, Biao ;

Wang, Liang .

CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (10) :2823-2828

[30] Rhodium-catalyzed regioselective amidation of indoles with sulfonyl azides via C-H bond activation [J].

Shi, Jingjing ;

Zhou, Bing ;

Yang, Yaxi ;

Li, Yuanchao .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (45) :8953-8955

← 1 2 3 4 5 →