Dual C–H Aminotrideuteromethylthiolation of N-Alkyl Indoles with Alkylamines and CD3SSO3Na

Herein, we describe a versatile and region-selective 2,3-aminotrideuteromethylthiolation of N-alkyl indoles with alkylamines and CD₃SSO₃Na using NaIO₄ as reaction mediator. This strategy is exemplified in the preparation of 33 SCD₃-labeled indoles, late-stage indolyltrideuteromethylthiolation of drug intermediates, and product derivatization. Initial mechanistic investigations have verified that NaIO₄ could be converted to I₂ by CD₃SSO₃Na and that alkylamine contributes to the activation of the Bunte salts.