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.

Atslēgas vārdi
sulfur dioxide, solvent, bora-ene reaction, sulfone synthesis
DOI
10.1016/j.tetlet.2017.05.097
Hipersaite
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, 2727.-2731.lpp. ISSN 0040-4039. Pieejams: doi:10.1016/j.tetlet.2017.05.097

Publikācijas valoda
English (en)