N<sup>2</sup>-Selective β-Thioalkylation of Benzotriazoles with Alkenes
Li-Li Zhu, Lifang Tian, Kunhui Sun, Yiwen Li, Guanglu Liu, Bin Cai, Hui Zhang, Yahui Wang
Abstract
Herein, N2-selective β-thioalkylation of benzotriazoles with unactivated alkenes and styrenes is reported. The N2-selective β-thioalkylation of benzotriazoles is highly stereospecific and works under simple and mild conditions, exhibiting excellent functional group tolerance. The high N2-selectivity is a consequence of the combination of hydrogen bonding and Lewis acid/base activation, which reverses the N2-position to be favored for alkylation.
Topics & Concepts
ChemistryStereospecificitySelectivityAlkylationLewis acids and basesAlkeneMedicinal chemistryOrganic chemistryCatalysisSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions