Difluoromethylene Phosphabetaine as an Equivalent of Difluoromethyl Carbanion
Organic Letters2014Vol. 16(23), pp. 6256–6259
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Vitalij V. Levin, Alexey L. Trifonov, Artem A. Zemtsov, Марина И. Стручкова, Dmitry E. Arkhipov, Alexander D. Dilman
Abstract
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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