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Methylthiolation for Electron‐Rich Heteroarenes with DMSO‐TsCl
Author(s) -
Zhang LeiYang,
Wu YueHua,
Wang NaiXing,
Gao XueWang,
Yan Zhan,
Xu BaoCai,
Liu Ning,
Wang BoZhou,
Xing Yalan
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100001
Subject(s) - chemistry , regioselectivity , mechanism (biology) , combinatorial chemistry , scalability , computational chemistry , organic chemistry , catalysis , computer science , database , philosophy , epistemology
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.