Visible-Light-Promoted Regioselective Hydroborylation of Ketene Dithioacetals with NHC-Boranes

J Org Chem. 2023 Nov 3;88(21):15151-15158. doi: 10.1021/acs.joc.3c01642. Epub 2023 Oct 18.

Abstract

NHC-boranes have been treated as a reliable source of boryl radicals. In this study, regioselective hydroborylation of ketene dithioacetals with NHC-borane was achieved under mild conditions via a visible-light-promoted radical chain process using thiophenol as a proton donor and hydrogen atom transfer. This protocol features a low-cost catalyst, good functional group tolerance, a relatively broad range of substrate scope, and good to excellent yields. Moreover, mechanism of this hydroborylation reaction was preliminarily studied.