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Regioselective Cleavage and Reconfiguration of C–S Bonds with Diazo Compounds

Huan Li, Zhimin Xia, Lewan Li, Jie Zeng, Jian Lv, Haifeng Wang, Shuang‐Xi Gu, Fen‐Er Chen

2024Organic Letters10 citationsDOI

Abstract

A coupling reaction between diazo compounds and phenyl benzyl sulfide catalyzed by TfOH has been reported. This reaction can synthesize important α-arylthio carbonyl compounds via regioselective cleavage and reconfiguration of C-S bonds, and various functional groups were tolerant to the reaction conditions. Mechanistic studies have conclusively established that the pivotal intermediate in the reaction was meticulously investigated through spectroscopic evidence, complemented by rigorous control experiments.

Topics & Concepts

ChemistryDiazoRegioselectivityCleavage (geology)Control reconfigurationBond cleavageStereochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisComputer scienceEngineeringFracture (geology)Geotechnical engineeringEmbedded systemSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions
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