Synthesis of allyl sulfones from potassium allyltrifluoroborates |
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Authors: | Agnese Stikute Jevge?ija Lugi?ina Māris Turks |
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Institution: | Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, Paula Valdena Str. 3, Riga LV-1048, Latvia |
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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 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. |
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Keywords: | Sulfur dioxide Potassium allyltrifluoroborates Potassium 3-((allylsulfinyl)oxy)trifluoroborate Sulfones |
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