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

[1] Recent developments and perspectives in palladium-catalyzed cyanation of aryl halides: synthesis of benzonitriles [J].

Anbarasan, Pazhamalai ;

Schareina, Thomas ;

Beller, Matthias .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5049-5067

[2]

[Anonymous], 1970, Chemistry of the Cyano Group

[3]

[Anonymous], 1884, Berichte Dtsch. Chem. Ges, DOI DOI 10.1002/CBER.18840170219

[4] The palladium-catalyzed desulfitative cyanation of arenesulfonyl chlorides and sodium sulfinates [J].

Chen, Jianbin ;

Sun, Yang ;

Liu, Bin ;

Liu, Dongfang ;

Cheng, Jiang .

CHEMICAL COMMUNICATIONS, 2012, 48 (03) :449-451

[5] 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

[6] Direct Transformation of N,N-Dimethylformamide to -CN: Pd-Catalyzed Cyanation of Heteroarenes via C-H Functionalization [J].

Ding, Shengtao ;

Jiao, Ning .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (32) :12374-12377

[7]

Fatiadi A.J., 1983, Preparation and Synthetic Applications of Cyano Compounds

[8] RADICAL REACTIONS OF ARENEDIAZONIUM IONS - AN EASY ENTRY INTO THE CHEMISTRY OF THE ARYL RADICAL [J].

GALLI, C .

CHEMICAL REVIEWS, 1988, 88 (05) :765-792

[9] THE SANDMEYER REACTION [J].

HODGSON, HH .

CHEMICAL REVIEWS, 1947, 40 (02) :251-277

[10] Palladium-catalyzed cyclization of o-alkynyltrifluoroacetanilides followed by isocyanide insertion: synthesis of 2-substituted 1H-indole-3-carboxamides [J].

Hu, Ziwei ;

Liang, Dongdong ;

Zhao, Jiaji ;

Huang, Jinbo ;

Zhu, Qiang .

CHEMICAL COMMUNICATIONS, 2012, 48 (59) :7371-7373

← 1 2 3 4 →