TY - JOUR A1 - Wang, Fei A1 - Li, Lingchun A1 - Ni, Chuanfa A1 - Hu, Jinbo T1 - Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine JF - Beilstein Journal of Organic Chemistry PY - 2014/// VL - 10 SP - 344 EP - 351 SN - 1860-5397 DO - 10.3762/bjoc.10.32 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.10.32 KW - (chlorodifluoromethyl)trimethylsilane KW - difluorocarbene KW - gem-difluoroolefin KW - organo-fluorine KW - Wittig reaction KW - ylide N2 - Background: 1,1-Difluoroalkenes cannot only be used as valuable precursors for organic synthesis, but also act as bioisosteres for enzyme inhibitors. Among various methods for their preparation, the carbonyl olefination with difluoromethylene phosphonium ylide represents one of the most straightforward methods.Results: The combination of (chlorodifluoromethyl)trimethylsilane (TMSCF2Cl) and triphenylphosphine (PPh3) can be used for the synthesis of gem-difluoroolefins from carbonyl compounds. Comparative experiments demonstrate that TMSCF2Cl is superior to (bromodifluoromethyl)trimethylsilane (TMSCF2Br) and (trifluoromethyl)trimethylsilane (TMSCF3) in this reaction.Conclusion: Similar to many other Wittig-type gem-difluoroolefination reactions in the presence of PPh3, the reaction of TMSCF2Cl with aldehydes and activated ketones is effective. ER -