Direct Synthesis of Amides from Benzonitriles and Benzylic Alcohols via a KOt-Bu-Mediated MPV-type Hydrogen Transfer Process

Meerwein-Ponndorf-Verley (MPV)-type reduction between benzonitriles and benzylic alcohols under transitionmetal-free conditions has been demonstrated for the first time. Using simple KOt-Bu as the base, various benzonitriles can be efficiently reduced by benzylic alcohols via hydrogen transfer reduction, and the resultant phenyl imine can react further with benzylic alcohols to give amides as the final product in which both the alcohols and the nitriles are incorporated. Preliminary mechanistic investigations indicated that the reaction may go through multiple MPV-type hydrogen transfer processes.

Automated summary

This study demonstrates for the first time the feasibility of Meerwein-Ponndorf-Verley (MPV)-type reduction between benzonitriles and benzylic alcohols under transition-metal-free conditions. The reaction can be efficiently carried out using simple KOt-Bu as the base, and the resulting product is an amide incorporating both the alcohols and the nitriles.