Photoredox‐Controlled β‐Regioselective Radical Hydroboration of Activated Alkenes with NHC‐Boranes
Congjun Zhu, Congjun Zhu, Jie Dong, Xueting Liu, Liuzhou Gao, Yue Zhao, Jin Xie, Shuhua Li, Chengjian Zhu, Chengjian Zhu
Abstract
Abstract In this Communication, we report an unprecedented β‐regioselective radical inverse hydroboration (compared with ionic hydroboration) of α,β‐unsaturated amides with NHC‐BH 3 enabled by photoredox catalysis. Density functional theory (DFT) calculations show that the unique photoredox cycle is a key factor to control the β‐regioselective radical hydroboration, by lowering the energy barrier in comparison with other pathways. This protocol provides a general and convenient route to construct a wide range of structurally diverse β‐borylated amides in synthetically useful yields under mild conditions.
Topics & Concepts
HydroborationRegioselectivityChemistryBoranesCombinatorial chemistryOrganic chemistryCatalysisBoronOrganoboron and organosilicon chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods