Photochemical singlet carbene insertion into alkenylboronic acids

Abstract

A visible-light induced singlet carbene insertion reaction of alkenylboronic acids with aryl diazoacetates has been disclosed. Mechanistic studies indicate that the reaction proceeds via singlet carbene nucleophilic attack on alkenylboronic acid to form an ylide, followed by a 1,2-alkenyl migration, deboration and deuteration with D₂O, enabling efficient deuterium labeling.