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Electrochemical Oxidative Syntheses of NH‐Sulfoximines, NH‐Sulfonimidamides and Dibenzothiazines via Anodically Generated Hypervalent Iodine Intermediates

Xianqiang Kong, Long Lin, Xiao‐Hui Chen, Yiyi Chen, Wei Wang, Bo Xu

2021ChemSusChem27 citationsDOI

Abstract

Herein, we report a general method for the synthesis of NH-sulfoximines and NH-sulfonimidamides through direct electrochemical oxidative catalysis involving an iodoarene(I)/iodoarene(III) redox couple. In addition, dibenzothiazines can be synthesized from [1,1'-biaryl]-2-sulfides under standard conditions. Notably, only a catalytic amount of iodoarene is required for the generation in situ of an active hypervalent iodine catalyst, which avoids the need for an excess of a hypervalent iodine reagent relative to conventional approaches. Moreover, this protocol features broad substrate scope and wide functional group tolerance, delivering the target compounds with good-to-excellent yields even for a scale of more than 10 g.

Topics & Concepts

Hypervalent moleculeReagentChemistryCatalysisIodineElectrochemistryCombinatorial chemistrySubstrate (aquarium)RedoxInorganic chemistryOrganic chemistryElectrodePhysical chemistryOceanographyGeologySynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
Electrochemical Oxidative Syntheses of NH‐Sulfoximines, NH‐Sulfonimidamides and Dibenzothiazines via Anodically Generated Hypervalent Iodine Intermediates | Litcius