General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP

被引：93

作者：

Zhang, Xingjie ^{[1
]}

Xia, Aiyou ^{[1
]}

Chen, Haoyi ^{[1
]}

Liu, Yuanhong ^{[1
]}

机构：

[1] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 08期

基金：

中国国家自然科学基金;

关键词：

ARYL CHLORIDES; AROMATIC HALIDES; IN-SITU; HETEROARYL CHLORIDES; COMPLEXES; BROMIDES; AMINATION; SCOPE; ANNOUNCEMENT; LIMITATIONS;

D O I：

10.1021/acs.orglett.7b00732

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and general nickel-catalyzed cyanation of hetero(aryl) Chlorides using less toxic Zn(CN)(2) as the cyanide source has been developed. The reaction relies on the use of inexpensive NiCl2.6H(2)O/dppf/Zn, as the catalytic system, and DMAP as the additive, allowing the cyanation to occur :under mild reaction conditions (50-80 degrees C) with wide functional group tolerance. DMAP was found to be crucial for successful transformation, and the reaction likely proceeds via a Ni(0)/Ni(II) catalysis based on mechanistic studies. The method was also successfully extended to aryl bromides and aryl iodides.

引用

页码：2118 / 2121

页数：4

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