Visible-Light-Promoted Site-Selective <i>N</i><sup>1</sup>-Alkylation of Benzotriazoles with α-Diazoacetates
Jingya Yang, Jiaokui Duan, Ganggang Wang, Hongyan Zhou, Ben Ma, Chengqi Wu, Jianliang Xiao
Abstract
A visible-light-promoted highly site-selective N1-alkylation of benzotriazoles with diazo compounds has been achieved under mild and metal-free conditions. Using cheap, readily available p-benzoquinone (PBQ) as a catalyst, a wide range of benzotriazoles and diazo compounds are reacted, providing N1-alkylated benzotriazoles in moderate to excellent yields with excellent N1-selectivities. Preliminary mechanistic studies suggest that a radical process accounts for the exclusive site-selectivity of this transformation.
Topics & Concepts
AlkylationChemistryDiazoSelectivityCatalysisPhotochemistryMetalCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsRadical Photochemical Reactions