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Defluorinative Thiolation of gem-Difluoroalkenes by Convergent Paired Electrolysis

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c02235

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We have successfully developed a convergent paired electrolysis strategy for defluorinative thiolation using thiols and gem-difluoroalkenes as precursors. This protocol shows excellent tolerance towards a wide range of functional groups, demonstrated by successful late-stage defluorothiolation of complex molecules. Additionally, this strategy enables gram-scale synthesis by efficiently utilizing both anodic oxidation and cathodic reduction processes.
Herein, we have successfully developed a convergent pairedelectrolysisstrategy for the defluorinative thiolation process utilizing thiolsand gem-difluoroalkenes as precursors. This protocolexhibits remarkable tolerance toward a wide range of functional groups,as exemplified by the successful late-stage defluorothiolation ofcomplex molecules. Additionally, this strategy is amenable to gram-scalesynthesis, making use of both anodic oxidation and cathodic reductionprocesses in an efficient manner. Several control studies were conductedand suggested a convergent paired electrolysis mechanism.

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