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.
Fields of Study & Subjects
Advanced Synthetic Organic Chemistry
Organoboron and organosilicon chemistry
Catalytic C–H Functionalization Methods
Publication details
- Journal / source
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Volume
- 65
- Issue
- 27
- Pages
- e4999077–e4999077
- Publication date
- 19 May 2026
- Language
- EN