Copper-catalyzed carbonylative Hiyama-coupling of alkyl bromides and aryl trimethoxysilanes toward arylalkyl ketones

Abstract

Ketones, especially arylalkyl ketones, represent an important structural motif with wide applications in various areas. Herein, we report a copper-catalyzed carbonylative cross-coupling reaction between alkyl bromides and arylsilanes for the synthesis of ketones. By employing a commercially available copper salt in combination with an NHC ligand as the catalyst system, a variety of the desired arylalkyl ketones were obtained in moderate to good yields with broad substrate scope and excellent functional group tolerance. This catalytic system overcomes the sluggish oxidative addition of alkyl bromides, effectively suppresses the undesired dehalogenation side reactions, and also minimizes the competing direct Hiyama coupling.