Synthesis of Allyl Sulfones from Potassium Allyltrifluoroborates
Tetrahedron Letters
2017
Agnese Stikute,
Jevgeņija Lugiņina,
Māris Turks
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 sulfinyloxytrifluoroborates
to produce the corresponding 2,4-dinitrophenylsulfone. The developed method allows
the transformation of potassium allyltrifluoroborates into allyl sulfones.
Keywords
sulfur dioxide, solvent, bora-ene reaction, sulfone synthesis
DOI
10.1016/j.tetlet.2017.05.097
Hyperlink
http://www.sciencedirect.com/science/article/pii/S0040403917307086?via%3Dihub
Stikute, A., Lugiņina, J., Turks, M. Synthesis of Allyl Sulfones from Potassium Allyltrifluoroborates. Tetrahedron Letters, 2017, Vol.58, Iss.28, pp.2727-2731. ISSN 0040-4039. Available from: doi:10.1016/j.tetlet.2017.05.097
Publication language
English (en)