Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization

• Main Authors: Xu, Wengang, Yoshikai, Naohiko
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2018
• Subjects: C–H Bond Functionalization; Arylation Reactions
• Online Access: https://hdl.handle.net/10356/86808; http://hdl.handle.net/10220/44261
• Institution: Nanyang Technological University

Pivalophenone N–H imine has been found to serve as a prominent substrate for directed C–H alkylation and arylation reactions with alkyl bromides and aryl chlorides, respectively, under cobalt–N-heterocyclic carbene (NHC) catalysis. Unlike the case of the parent pivalophenone imine, the increased steric bulk of the resulting ortho-substituted pivalophenone imines allows them to undergo clean imine-to-nitrile conversion under peroxide photolysis or aerobic copper catalysis conditions. Overall, these two-step transformations offer convenient synthetic methods for ortho-functionalized benzonitriles.