Synthesis of functionalized dialkyl ketones from carboxylic acid derivatives and alkyl halides.

ABSTRACT: Unsymmetrical dialkyl ketones can be directly prepared by the nickel-catalyzed reductive coupling of carboxylic acid chlorides or (2-pyridyl)thioesters with alkyl iodides or benzylic chlorides. A wide variety of functional groups are tolerated by this process, including common nitrogen protecting groups and C-B bonds. Even hindered ketones flanked by tertiary and secondary centers can be formed. The mechanism is proposed to involve the reaction of a (L)Ni(alkyl)(2) intermediate with the carboxylic acid derivative.

SUBMITTER: Wotal AC 

PROVIDER: S-EPMC3308727 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature