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Base-Promoted Sulfur Arylation of Sulfenamides to Oxonium Aryne Precursors: Chemoselective Synthesis of Sulfilimines and <i>o</i>-Sulfanylanilines

Liang Chen, Sheng Fang, Jialin Song, Qiong Hu, Shang‐Shi Zhang, Bing Shu

2024The Journal of Organic Chemistry7 citationsDOI

Abstract

In this study, a metal-free and efficient method for the synthesis of sulfilimines and o -sulfanylanilines in high yields with excellent chemoselectivities from oxonium aryne precursors with sulfenamides has been developed. This method features mild reaction conditions, simple operations, a general substrate scope, and good tolerance of functional groups. In addition, scale-up synthesis, related applications, and preliminary mechanistic explorations were also investigated.

Topics & Concepts

Oxonium ionAryneBase (topology)ChemistrySulfurCombinatorial chemistryOrganic chemistryMathematicsMathematical analysisIonCatalytic Alkyne ReactionsCyclization and Aryne ChemistrySulfur-Based Synthesis Techniques
Base-Promoted Sulfur Arylation of Sulfenamides to Oxonium Aryne Precursors: Chemoselective Synthesis of Sulfilimines and <i>o</i>-Sulfanylanilines | Litcius