Cobalt-Catalyzed Aerobic Oxidative C-H/C-H Cross-Coupling of Unactivated Arenes for the Synthesis of Biaryls

被引：36

作者：

Lv, Ningning ^{[1
]}

Chen, Zhengkai ^{[2
]}

Liu, Yue ^{[1
]}

Liu, Zhanxiang ^{[1
]}

Zhang, Yuhong ^{[1
,3
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

[2] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China

[3] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 18期

关键词：

MOLECULAR-OXYGEN; BOND FORMATION; NATURAL-PRODUCTS; DIRECTING GROUPS; HETEROARENES; N-OXIDES; FUNCTIONALIZATION; ACTIVATION; ARYLATION; HETEROARYLATION;

D O I：

10.1021/acs.orglett.8b02526

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient protocol for the synthesis of 2,2'-difunctional biaryls from readily available benzamides and oximes by Co(OAc)(2)center dot 4H(2)O catalysis has been developed. The catalytic cycle that includes aerobic oxidation of Co(I) to Co(III) is successfully achieved for the first time through dual-chelation-assisted C-H/C-H coupling with the assistance of catalytic Mn(acac)(3). The catalytic system exhibits powerful reactivity and tolerates a large number of sensitive functional groups.

引用

页码：5845 / 5848

页数：4

共 57 条

[41]

Stuart DR, 2007, SCIENCE, V316, P1172, DOI 10.1126/science.1141956

[42] Copper-Catalyzed Formation of -Alkoxycycloalkenones from N-Tosylhydrazones [J].

Su, Naijing ;

Theorell, Juliana A. ;

Wink, Donald J. ;

Driver, Tom G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (44) :12942-12946

[43] Cobalt-Catalyzed Oxidative C-H/C-H Cross-Coupling between Two Heteroarenes [J].

Tan, Guangying ;

He, Shuang ;

Huang, Xiaolei ;

Liao, Xingrong ;

Cheng, Yangyang ;

You, Jingsong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (35) :10414-10418

[44] C-H functionalization by high-valent Cp*Co(III) catalysis [J].

Wang, Shan ;

Chen, Shan-Yong ;

Yu, Xiao-Qi .

CHEMICAL COMMUNICATIONS, 2017, 53 (22) :3165-3180

[45] High-Valent-Cobalt-Catalyzed C-H Functionalization Based on Concerted Metalation-Deprotonation and Single-Electron-Transfer Mechanisms [J].

Wei, Donghui ;

Zhu, Xinju ;

Niu, Jun-Long ;

Song, Mao-Ping .

CHEMCATCHEM, 2016, 8 (07) :1242-1263

[46] Pd(OAc)2-Catalyzed Oxidative C-H/C-H Cross-Coupling of Electron-Deficient Polyfluoroarenes with Simple Arenes [J].

Wei, Ye ;

Su, Weiping .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (46) :16377-16379

[47] [RhIIICp*]-Catalyzed Dehydrogenative Aryl?Aryl Bond Formation [J].

Wencel-Delord, Joanna ;

Nimphius, Corinna ;

Patureau, Frederic W. ;

Glorius, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (09) :2247-2251

[48] Carbon-carbon bond formation through double Sp2 C-H activations:: Synthesis of ferrocenyl oxazoline derivatives [J].

Xia, Ji-Bao ;

You, Shu-Li .

ORGANOMETALLICS, 2007, 26 (20) :4869-4871

[49] Oxidative C-H/C-H Coupling Reactions between Two (Hetero)arenes [J].

Yang, Yudong ;

Lan, Jingbo ;

You, Jingsong .

CHEMICAL REVIEWS, 2017, 117 (13) :8787-8863

[50] Catalytic Dehydrogenative Cross-Coupling: Forming Carbon-Carbon Bonds by Oxidizing Two Carbon-Hydrogen Bonds [J].

Yeung, Charles S. ;

Dong, Vy M. .

CHEMICAL REVIEWS, 2011, 111 (03) :1215-1292

← 1 2 3 4 5 6 →