Advances in C(sp3)-H Bond Functionalization via Radical Processes

被引：36

作者：

Zhang, Tong ^{[1
,2
]}

Wu, Yue-Hua ^{[1
,2
]}

Wang, Nai-Xing ^{[1
,2
]}

Xing, Yalan ^{[3
]}

机构：

[1] Chinese Acad Sci, Tech Inst Phys & Chem, Beijing 100190, Peoples R China

[2] Chinese Acad Sci, Univ Chinese Acad Sci, Beijing 100190, Peoples R China

[3] William Paterson Univ New Jers, Dept Chem, Wayne, NJ 07470 USA

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 24期

基金：

中国国家自然科学基金;

关键词：

C(sp(3))-H functionalization; oxidative coupling; transition-metal catalyzed; step economy; green chemistry; SP(3) C-H; DEHYDROGENATIVE-COUPLING CDC; CARBOXYLIC-ACIDS; ALKYNES; ETHERS; VINYLARENES; ACCESS; HETEROARYLATION; ACTIVATION; ALKYLATION;

D O I：

10.1055/s-0039-1690674

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C(sp(3))-H Bonds are the most common structures in organic molecules. In recent years, the direct functionalization of C(sp(3))-H bonds has attracted wide attention and made significant progress. This review mainly focuses on C(sp(3))-H bond functionalization of alkanes with or without functional groups via radical processes reported since 2017. In particular, three methods of generating free radicals are discussed: the use of a radical initiator such as TBHP or DTBP; photocatalysis, and via 1,5-hydrogen atom transfer (1,5-HAT).

引用

页码：4531 / 4548

页数：18

共 84 条

[1] Photoredox-Catalyzed Site-Selective α-C(sp3)-H Alkylation of Primary Amine Derivatives [J].

Ashley, Melissa A. ;

Yamauchi, Chiaki ;

Chu, John C. K. ;

Otsuka, Shinya ;

Yorimitsu, Hideki ;

Rovis, Tomislav .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (12) :4002-4006

[2] Copper-catalyzed remote C(sp3)-H azidation and oxidative trifluoromethylation of benzohydrazides [J].

Bao, Xu ;

Wang, Qian ;

Zhu, Jieping .

NATURE COMMUNICATIONS, 2019, 10 (1)

[3] Doubly Regioselective C-H Hydroarylation of Unsymmetrical Alkynes Using Carboxylates as Deciduous Directing Groups [J].

Biafora, Agostino ;

Khan, Bilal A. ;

Bahri, Janet ;

Hewer, Joachim M. ;

Goossen, Lukas J. .

ORGANIC LETTERS, 2017, 19 (05) :1232-1235

[4] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].

Chen, Xiao ;

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115

[5] Copper-Catalyzed Cross-Dehydrogenative Coupling (CDC) of Alkynes and Benzylic C-H Bonds [J].

Correia, Camille A. ;

Li, Chao-Jun .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (09) :1446-1450

[6] Ru(II)-Catalyzed Oxidative Heck-Type Olefination of Aromatic Carboxylic Acids with Styrenes through Carboxylate-Assisted C-H Bond Activation [J].

Dana, Suman ;

Mandal, Anup ;

Sahoo, Harekrishna ;

Mallik, Sumitava ;

Grandhi, Gown Sankar ;

Baidya, Mahiuddin .

ORGANIC LETTERS, 2018, 20 (03) :716-719

[7] Ruthenium-catalyzed oxidative cross-coupling of chelating arenes and cycloalkanes [J].

Deng, Guojun ;

Zhao, Liang ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (33) :6278-6282

[8] Eosin Y as a Direct Hydrogen-Atom Transfer Photocatalyst for the Functionalization of C-H Bonds [J].

Fan, Xuan-Zi ;

Rong, Jia-Wei ;

Wu, Hao-Lin ;

Zhou, Quan ;

Deng, Hong-Ping ;

Da Tan, Jin ;

Xue, Cheng-Wen ;

Wu, Li-Zhu ;

Tao, Hai-Rong ;

Wu, Jie .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (28) :8514-8518

[9] Mild metal-catalyzed C-H activation: examples and concepts [J].

Gensch, T. ;

Hopkinson, M. N. ;

Glorius, F. ;

Wencel-Delord, J. .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (10) :2900-2936

[10] Iron(II)-Catalyzed Site-Selective Functionalization of Unactivated C(sp3)-H Bonds Guided by Alkoxyl Radicals [J].

Guan, Honghao ;

Sun, Shutao ;

Mao, Ying ;

Chen, Lei ;

Lu, Ran ;

Huang, Jiancheng ;

Liu, Lei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (35) :11413-11417

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