Synthesis of 5-(Trifluoromethyl)-2,5-dihydro-1,2λ⁵-oxaphospholes by a One-Pot Three-Component Reaction

Abstract

A series of trifluoromethyl-substituted 1,2λ⁵-oxaphospholes were prepared in yields of up to 95% by a one-pot three-component­ reaction under mild conditions. The zwitterionic intermediate generated by attack of triphenylphosphine on an alkyl propiolate reacts with an aryl or styryl trifluoromethyl ketone to form the 1,2λ⁵-oxaphosphole ring. All the new products were characterized by IR, NMR, and mass spectroscopy and the structure of one of them, ethyl 2,2,2-triphenyl-5-[(E)-2-phenylvinyl]-5-(trifluoromethyl)-2,5-dihydro-1,2λ⁵-oxaphosphole-4-carboxylate, was confirmed by X-ray single-crystal diffraction analysis.

Key words

heterocycles - phosphorus - fluorine - oxaphospholes - alkynes - ketones

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