t-BuOLi promoted regioselective N-thiolation of indoles with N-arylthio phthalimide
Zhitian Huang1, Hong Wei1, Qianyu Huang1
1Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai, PR China. ghsong@ecust.edu.cn.
Abstract:
The selective N-thiolation of indole substrates poses a challenge due to their diminished nucleophilicity at nitrogen. Herein, we present a novel method for the thiolation of the NH group in indole derivatives by using N-arylthio phthalimide as the sulfur source, t-BuOLi as the base and MeCN as the solvent. The process was successfully conducted under transition metal catalyst-free and room temperature conditions with a high product yield and a short reaction time. The developed protocol exhibited excellent regioselectivity and broad substrate tolerance in the preparation of N-thioindoles with diverse functional groups.
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