Nickel-Catalyzed Cyanation of Unactivated Alkyl Chlorides or Bromides with Zn(CN)2

Aiyou Xia; Xin Xie; Haoyi Chen; Jidong Zhao; Chunli Zhang; Yuanhong Liu

doi:10.1021/acs.orglett.8b03539

Nickel-Catalyzed Cyanation of Unactivated Alkyl Chlorides or Bromides with Zn(CN)₂

Org Lett. 2018 Dec 7;20(23):7735-7739. doi: 10.1021/acs.orglett.8b03539. Epub 2018 Nov 15.

Authors

Aiyou Xia¹, Xin Xie¹, Haoyi Chen¹, Jidong Zhao¹, Chunli Zhang¹, Yuanhong Liu¹

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Lu , Shanghai 200032 , People's Republic of China.

PMID: 30431281
DOI: 10.1021/acs.orglett.8b03539

Abstract

A nickel-catalyzed cyanation of unactivated secondary alkyl chlorides or bromides using less toxic Zn(CN)₂ as the cyanide source has been developed. The reaction features the use of air-stable and inexpensive NiCl₂·6H₂O or Ni(acac)₂ as the precatalysts and offers an efficient synthesis of a broad range of alkyl nitriles. Cyanation of primary alkyl chlorides or bromides was also achieved by reaction with Zn(CN)₂ in the presence of n-Bu₄NCl without the need of nickel catalyst.

Publication types

Research Support, Non-U.S. Gov't