Energy-Transfer-Enabled Radical Acylation Using Free Alkyl Boronic Acids through Photo and NHC Dual Catalysis

Cross-coupling reactions have been well received as one of the most popular protocols for ketone synthesis. As an important coupling partner, bench-stable and commercially available alkyl boronic acids are widely used in transition metal catalysis, but they are rarely utilized as radical precursors...

Full description

Saved in:
Bibliographic Details
Published in:ACS catalysis 2024-03, Vol.14 (5), p.3181-3190
Main Authors: Liu, Wan-Cong, Zhang, Xiang, Chen, Lin, Zeng, Rong, Tian, Yuan-Hang, Ma, En-Dian, Wang, Ya-Peng, Zhang, Bin, Li, Jun-Long
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Cross-coupling reactions have been well received as one of the most popular protocols for ketone synthesis. As an important coupling partner, bench-stable and commercially available alkyl boronic acids are widely used in transition metal catalysis, but they are rarely utilized as radical precursors for acylative coupling reactions. Herein, we reported an energy-transfer-enabled radical acylation using free alkyl boronic acids via NHC/photo dual catalysis. This protocol could efficiently promote the Suzuki-type cross-coupling between alkyl boronic acids and acyl imidazoles as well as the multicomponent alkylacylations of alkenes, thus producing various ketones with structural diversity. Additionally, ketone products can readily transform into a large number of structurally interesting fine chemicals. Preliminary mechanistic studies shed light on the unique radical reaction mechanism.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.3c06027