Inverse Hydroboration of Imines with NHC-Boranes Is Promoted by Diphenyl Disulfide and Visible Light
Takuji Kawamoto, Tsubasa Morioka, Kohki Noguchi, Dennis P. Curran, Akio Kamimura
Abstract
We describe a simple and efficient procedure for nucleophilic borylation of imines in the absence of a photoredox catalyst. Visible light irradiation of an acetonitrile solution of an imine, an NHC-borane, and diphenyl disulfide (10 mol %) provides various stable α-amino NHC-boranes in good yields. The reaction proceeds via addition of a nucleophilic boryl radical to an imine, followed by hydrogen abstraction from thiophenol, which is generated from NHC-borane and diphenyl disulfide.
Topics & Concepts
ChemistryBoranesThiophenolNucleophileImineBoraneBorylationPhotochemistryCarbon disulfideCatalysisOrganic chemistryBoronAlkylArylOrganoboron and organosilicon chemistryRadical Photochemical ReactionsSulfur-Based Synthesis Techniques