Catalytic Selective Deoxygenation and Deamination of Amides to Access Alkenes

Abstract

ABSTRACT Amide derivatizations are important and useful transformations in organic chemistry, owing to the ready accessibility of amides. However, reported methodologies to date have been limited to either deoxygenative or deaminative pathways; the direct, single‐step conversion of amides into hydrocarbons has remained elusive. In this work, by employing 9‐borabicyclo[3.3.1]nonane (9‐BBN) as the reductant and Cp 2 ZrCl 2 as a precatalyst, we demonstrate that amides can be efficiently converted to alkenes under simple and mild conditions, which represents the third mode of amide derivatization after deoxygenation and deamination. Mechanistic investigations reveal that 9‐BBN is crucial for the tandem C─O and C─N cleavage. This transformation links the two fundamental functional groups such that the richness of amide retrosynthesis is applied to alkenes.