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Updated: Jul 12, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
PhI(OAc)2-Mediated Regioselective Hydrothiolation of Allenamides with Thiophenol via a Radical Process: Synthesis of
Kun Zhao1, Qingsong Liu1, Song Cheng1
1Key Laboratory of Basic Chemistry of the State Ethnic Commission, School of Chemistry and Environment, Southwest Minzu University, Chengdu, Sichuan 610041, P. R. China.
Abstract:
An efficient PhI(OAc)2-mediated regioselective hydrothiolation of allenamides with thiophenol via a radical process was developed to create a workable route to vinyl sulfides. The reaction exhibits a good functional group tolerance and high efficiency, affording the products in good to excellent yields. Mechanistic investigations indicated that the radical cascade proceeds through an allyl radical intermediate, which is formed via the addition of the PhS radical to the central carbon of allenamides. Moreover, the reaction was also efficient with selenophenol, providing the corresponding product, vinyl selenide, in a 99% yield.
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