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Synthesis of <i>ortho</i>-Phenolic Sulfilimines via an Intermolecular Sulfur Atom Transfer Cascade Reaction

Feng Xiong, Yingying Zuo, Yinan Song, Linxing Zhang, Xinhao Zhang, Shaojian Xu, Yan Ren

2020Organic Letters29 citationsDOI

Abstract

-phenolic sulfilimines, sigmatropic rearrangements were introduced to the field of sulfilimine chemistry. Herein we report a N-H sulfenylation/[2,3]-sigmatropic rearrangement cascade reaction. This mild reaction enables commercially available thiols to serve as the sulfenylation reagent and generates water as the sole byproduct. Moreover, the reaction has a wide substrate scope and can be conducted on a gram scale with excellent reaction efficiency.

Topics & Concepts

ChemistryIntermolecular forceCascadeSulfurAtom (system on chip)Combinatorial chemistryCascade reactionComputational chemistryOrganic chemistryMoleculeCatalysisEmbedded systemComputer scienceChromatographySynthesis and Catalytic ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods