α,α-Difluoro-α-phenylsulfanylmethyl carbanion equivalent: a novel gem-difluoromethylenation of carbonyl compounds |
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Authors: | Manat Pohmakotr Kanhokthron Boonkitpattarakul Suwatchai Jarussophon Patoomratana Tuchinda |
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Institution: | a Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand b Department of Science Services, Ministry of Science and Technology, Rama VI Road, Bangkok 10400, Thailand |
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Abstract: | α,α-Difluoro-α-phenylsulfanyl-α-trimethylsilylmethane (PhSCF2SiMe3) has been demonstrated as an α,α-difluoro-α-phenylsulfanylmethyl carbanion equivalent. gem-Difluorophenylsulfanylmethylation of carbonyl compounds has been successfully achieved by using PhSCF2SiMe3 in the presence of TBAF in THF. The adducts have been converted to the corresponding gem-difluoroalkenes by a novel pyrolytic and/or FVP elimination of the β-hydroxy-α-phenylsufinyl derivatives under reduced pressure. |
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Keywords: | Difluoro(phenylsulfanyl)trimethylsilane gem-Difluoroalkene gem-Difluoromethylenation Fluoride-catalyzed reaction Carbonyl compounds |
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