Research ArticleChemistry

Electrochemical oxidative oxysulfenylation and aminosulfenylation of alkenes with hydrogen evolution

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Science Advances  03 Aug 2018:
Vol. 4, no. 8, eaat5312
DOI: 10.1126/sciadv.aat5312


Difunctionalization of alkenes is a valuable and versatile chemical transformation that could quickly build complex molecules. Extensive efforts have been made, and great achievement, such as Sharpless aminohydroxylation and dihydroxylation, has been reached. However, in marked contrast to the extensive research of aminohydroxylation and dihydroxylation, directly using thiophenols/thiols and O/N-nucleophiles to perform the difunctionalization of alkenes that form the C–S and C–O/N bonds together is still underexplored. The main issue is that thiophenols/thiols are often easily overoxidized to sulfoxides or sulphones under such essential oxidation conditions. We demonstrate an electrochemical oxidative oxysulfenylation and aminosulfenylation of alkenes. A critical feature of this transformation is that neither external chemical oxidants nor metal catalysts are required. This electrochemical oxidative synthetic strategy could also be applied for the hydroxysulfenylation and acyloxysulfenylation of alkenes.

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