Trideuteromethylthiolation through Reaction of Arynes, S -Methyl- d 3 Sulfonothioate with Sulfonamides or Amides: Access to Trideuteromethylated Sulfilimines

作者：Yuping Luo, Xiujuan He, Yike Jiang, Jie Li, Leifang Wu, Zhihua Cai, Lin He · 发表于：The Journal of Organic Chemistry · 年份：2024 · DOI：10.1021/acs.joc.4c01033 · 被引用次数：7 · 研究领域：Chemical Reactions and Isotopes、Organic and Inorganic Chemical Reactions、Chemical Reaction Mechanisms

A direct and practical three-component tandem reaction of arynes, S -methyl- d 3 sulfonothioate with sulfonamides or amides is developed. The reaction is highly efficient and chemoselective, which allows mild synthesis of trideuteromethylated sulfilimines with broad substrate scope and good functional group compatibility, giving the products in good to excellent yields with 92%–99% deuterium incorporation. Mechanism studies disclosed sulfenamide that generated in situ is the key intermediate for the reaction. This protocol provides potential method for introduction of -SCD 3 moiety for deuteration of marked drugs and drug candidates containing sulfilimine skeleton.