Palladium-Catalyzed C(sp2)-H Cyanation Using Tertiary Amine Derived Isocyanide as a Cyano Source

被引：141

作者：

Peng, Jiangling ^{[1
]}

Zhao, Jiaji ^{[1
]}

Hu, Ziwei ^{[1
]}

Liang, Dongdong ^{[1
]}

Huang, Jinbo ^{[1
]}

Zhu, Qiang ^{[1
]}

机构：

[1] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, State Key Lab Resp Dis, Guangzhou 510530, Guangdong, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 18期

基金：

美国国家科学基金会;

关键词：

C-H ACTIVATION; DIRECT TRANSFORMATION; INDOLES; N; N-DIMETHYLFORMAMIDE; ALDOXIMES; NITRILES; BONDS;

D O I：

10.1021/ol302372p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented palladium-catalyzed cyanation of aromatic C-H bonds by using tertiary amine derived isocyanide as a novel cyano source was developed. Cu(TFA)(2) was used as a requisite stoichiometric oxidant. Mechanistic studies suggest that a tertiary carbon cation-based intermediate Is involved following the C-N bond breakage.

引用

页码：4966 / 4969

页数：4

共 40 条

[11]

Ishihara K, 2002, ANGEW CHEM INT EDIT, V41, P2983, DOI 10.1002/1521-3773(20020816)41:16<2983::AID-ANIE2983>3.0.CO

[12]

2-X

[13] Chelation-Assisted Palladium-Catalyzed Direct Cyanation of 2-Arylpyridine C-H Bonds [J].

Jia, Xiaofei ;

Yang, Dongpeng ;

Zhang, Shouhui ;

Cheng, Jiang .

ORGANIC LETTERS, 2009, 11 (20) :4716-4719

[14] Synthesis of Amides via Palladium-Catalyzed Amidation of Aryl Halides [J].

Jiang, Huanfeng ;

Liu, Bifu ;

Li, Yibiao ;

Wang, Azhong ;

Huang, Huawen .

ORGANIC LETTERS, 2011, 13 (05) :1028-1031

[15] A New Combined Source of "CN" from N,N-Dimethylformamide and Ammonia in the Palladium-Catalyzed Cyanation of Aryl C-H Bonds [J].

Kim, Jinho ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (30) :10272-10274

[16]

Larock R. C, 1989, COMPREHENSIVE ORGANI

[17] Heterocycle Formation via Palladium-Catalyzed C-H Functionalization [J].

Mei, Tian-Sheng ;

Kou, Lei ;

Ma, Sandy ;

Engle, Keary M. ;

Yu, Jin-Quan .

SYNTHESIS-STUTTGART, 2012, 44 (12) :1778-1791

[18] Direct carboxamidation of indoles by palladium-catalyzed C-H activation and isocyanide insertion [J].

Peng, Jiangling ;

Liu, Lanying ;

Hu, Ziwei ;

Huang, Jinbo ;

Zhu, Qiang .

CHEMICAL COMMUNICATIONS, 2012, 48 (31) :3772-3774

[19] Iron-Facilitated Direct Oxidative C-H Transformation of Allylarenes or Alkenes to Alkenyl Nitriles [J].

Qin, Chong ;

Jiao, Ning .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (45) :15893-15895

[20] Preparation of quinazolino[3,2-a]quinazolines via a palladium-catalyzed three-component reaction of carbodiimide, isocyanide, and amine [J].

Qiu, Guanyinsheng ;

He, Yaohua ;

Wu, Jie .

CHEMICAL COMMUNICATIONS, 2012, 48 (32) :3836-3838

← 1 2 3 4 →