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.