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Abstract Potassium allyltrifluoroborates underwent a bora-ene reaction with sulfur dioxide in the absence of Lewis acid catalysts to give sulfinyloxy-trifluoroborates, which subsequently undergo alkylation with electrophiles to produce sulfones in… Click to show full abstract
Abstract Potassium allyltrifluoroborates underwent a bora-ene reaction with sulfur dioxide in the absence of Lewis acid catalysts to give sulfinyloxy-trifluoroborates, which subsequently undergo alkylation with electrophiles to produce sulfones in up to 91% yield. Benzyl halides and haloacetic acid derivatives can be used as the alkylation reagents while the Sanger reagent undergoes a SNAr reaction with sulfinyloxy-trifluoroborates to produce the corresponding 2,4-dinitrophenylsulfone. The developed method allows the transformation of potassium allyltrifluoroborates into allyl sulfones.
Journal Title: Tetrahedron Letters
Year Published: 2017
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