A General Method for Aminoquinoline-Directed, Copper-Catalyzed sp2 C-H Bond Amination

被引：150

作者：

Roane, James ^{[1
]}

Daugulis, Olafs ^{[1
]}

机构：

[1] Univ Houston, Dept Chem, Univ Pk, Houston, TX 77204 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 13期

关键词：

CARBON-HYDROGEN BONDS; ROOM-TEMPERATURE; INTERMOLECULAR AMINATION; AMIDATING REAGENTS; ARENES; PD; ALKYLAMINES; ANILINES; MILD; COMPATIBILITY;

D O I：

10.1021/jacs.6b01117

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An operationally simple and general method for copper-catalyzed, aminoquinoline-assisted amination of beta-C(sp(2))-H bonds of benzoic acid derivatives is reported. The reaction employs Cu(OAc)(2) or (CuOH)(2)CO3 catalysts, an amine coupling partner, and oxygen from air as a terminal oxidant. Exceptionally high generality with respect to amine coupling partners is observed. Specifically, primary and secondary aliphatic and aromatic amines, heterocycles, such as indoles, pyrazole, and carbazole, sulfonamides, as well as electron-deficient aromatic and heteroaromatic amines are competent coupling components.

引用

页码：4601 / 4607

页数：7

共 51 条

[1] Copper-Catalyzed para-Selective C-H Amination of Electron-Rich Arenes [J].

Berzina, Beatrise ;

Sokolovs, Igors ;

Suna, Edgars .

ACS CATALYSIS, 2015, 5 (11) :7008-7014

[2] EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].

BORDWELL, FG .

ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463

[3] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

[4] Recent Advances in Electrophilic Amination Reactions [J].

Corpet, Martin ;

Gosmini, Corinne .

SYNTHESIS-STUTTGART, 2014, 46 (17) :2258-2271

[5] 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

[6] Ortho vs Ipso: Site-Selective Pd and Norbornene-Catalyzed Arene C-H Amination Using Aryl Halides [J].

Dong, Zhe ;

Dong, Guangbin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (49) :18350-18353

[7] A Mild, Ferrocene-Catalyzed C-H Imidation of (Hetero)Arenes [J].

Foo, Klement ;

Sella, Eran ;

Thome, Isabelle ;

Eastgate, Martin D. ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (14) :5279-5282

[8] Copper-Catalyzed sp3 C-H Amination [J].

Gephart, Raymond T., III ;

Warren, Timothy H. .

ORGANOMETALLICS, 2012, 31 (22) :7728-7752

[9] Gold-Catalyzed Direct Amination of Arenes with Azodicarboxylates [J].

Gu, Liuqun ;

Neo, Boon Siong ;

Zhang, Yugen .

ORGANIC LETTERS, 2011, 13 (07) :1872-1874

[10] Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides [J].

Hartwig, John F. .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1534-1544

← 1 2 3 4 5 6 →