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Cyanide-Mediated Synthesis of Sulfones and Sulfonamides from Vinyl Sulfones

Tamal Roy, Ji-Woong Lee*

*Department of Chemistry, Nano-Science Center, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen, Denmark, Email: jiwoong.leechem.ku.dk

T. Roy, J.-W. Lee, Synlett, 2020, 31, 455-458.

DOI: 10.1055/s-0039-1690991 (free Supporting Information)


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Abstract

Cyanide mediates an in situ generation of a nucleophilic sulfinate ion from vinyl sulfones. Subsequent in situ S-alkylation provides sulfones in high yields. In the presence of N-bromosuccinimide, primary and secondary amines underwent sulfonamide formation.

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Key Words

cyanide, sulfonates, alkyl sulfones, benzyl sulfones, sulfonamides, vinyl sulfones, N-bromosuccinimide


ID: J72-Y2020