Difluoromethylene Phosphabetaine as an Equivalent of Difluoromethyl Carbanion | Zendy

Vitalij V. Levin | Zendy; Alexey L. Trifonov | Zendy; Artem A. Zemtsov | Zendy; Марина И. Стручкова | Zendy; Dmitry E. Arkhipov | Zendy; Alexander D. Dilman | Zendy

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Difluoromethylene Phosphabetaine as an Equivalent of Difluoromethyl Carbanion

Author(s) -

Vitalij V. Levin,

Alexey L. Trifonov,

Artem A. Zemtsov,

Марина И. Стручкова,

Dmitry E. Arkhipov,

Alexander D. Dilman

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol503225s

Subject(s) - chemistry , phosphonium , carbanion , electrophile , nucleophile , reagent , ylide , hydrolysis , substrate (aquarium) , phosphorus , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , oceanography , geology

A method for nucleophilic difluoromethylation of reactive Michael acceptors, aldehydes, and azomethines is described. The reaction is performed using the readily available and air-stable reagent difluoromethylene phosphabetaine. The process involves interaction of an electrophilic substrate with in situ generated difluorinated phosphonium ylide followed by hydrolysis of the carbon-phosphorus bond under mild conditions.

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