Open AccessNickel-Catalyzed Deaminative Cyanation: Nitriles and One-Carbon Homologation from Alkyl Amines
Author(s) -
Jianyu Xu,
J. Cameron Twitty,
Mary P. Watson
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c01959
Subject(s) - chemistry , cyanation , pyridinium , alkyl , nitrile , reagent , cyanide , nickel , organic chemistry , salt (chemistry) , catalysis , combinatorial chemistry , carbon fibers , materials science , composite number , composite material
A nickel-catalyzed deaminative cyanation of Katritzky pyridinium salts has been developed. When it is coupled with formation of the pyridinium salt from primary amines, this method enables alkyl amines to be converted to alkyl nitriles. A less toxic cyanide reagent, Zn(CN) 2 , is utilized, and diverse functional groups and heterocycles are tolerated. The method also enables a one-carbon homologation of alkyl amines via reduction of the nitrile products, in addition to many other potential transformations of the versatile nitrile group.