Methylthiolation for Electron‐Rich Heteroarenes with DMSO‐TsCl
Leiyang Zhang, Yue‐Hua Wu, Nai‐Xing Wang, Xue‐Wang Gao, Zhan Yan, Baocai Xu, Ning Liu, Bozhou Wang, Yalan Xing
Abstract
Abstract DMSO‐TsCl has been developed for direct methylthiolation of various electron‐rich heteroarenes (more than 40 examples) with high regioselectivity in moderate to excellent yields (up to 96 %). Especially, pyrroles, furans, and thiophenes can be efficiently mono‐methylthiolated. This practical method features scalable, metal‐free, mild conditions and is compatible with air and moisture. Several applications of methylthiolated products were demonstrated for the first time. Based on controlled experimental results, a plausible mechanism was proposed with two key intermediates involved in the mechanism being detected by HRMS.
Topics & Concepts
ChemistryRegioselectivityMechanism (biology)Combinatorial chemistryMetalComputational chemistryOrganic chemistryCatalysisPhilosophyEpistemologySulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsCatalytic C–H Functionalization Methods