One-pot synthesis of gem-difluorostyrenes from benzyl bromide via olefination of phosphonium ylide with difluorocarbene

A one-pot synthesis of gem-difluorostyrenes from benzyl bromide via sequential reactions is described. The sequential reactions, including quarternization of triphenylphosphine, deprotonation and the gem-difluoroolefination proceeded smoothly to afford the final products in good yields. •gem-Difluor...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2015-11, Vol.179, p.116-120
Main Authors: Deng, Xiao-Yun, Lin, Jin-Hong, Xiao, Ji-Chang
Format: Article
Language:English
Subjects:
Benzyl bromide
Difluorocarbene
gem-Difluorostyrenes
Olefination
One-pot
Phosphonium ylide
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Summary:A one-pot synthesis of gem-difluorostyrenes from benzyl bromide via sequential reactions is described. The sequential reactions, including quarternization of triphenylphosphine, deprotonation and the gem-difluoroolefination proceeded smoothly to afford the final products in good yields. •gem-Difluorostyrenes can be synthesized from benzyl bromide.•A sequential of reactions can occur in one-pot.•Decarboxylative synthesis of gem-difluorostyrenes proved to be successful. A new approach for the synthesis of gem-difluorostyrenes from benzyl bromide is described. Quaternization of triphenylphosphine with benzyl bromide to give phosphonium salts, deprotonation of the corresponding phosphonium salts to produce phosphonium ylide, and the subsequent olefination of phosphonium ylide with difluorocarbene generated from difluoromethylene phosphobetaine (Ph3P+CF2CO2−) by decarboxylation can occur smoothly in one-pot, furnishing the final gem-difluorostyrenes in good yields.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2015.06.009