Tetrahedron

Diethyl bromodifluoromethylphosphonate: a highly efficient and environmentally benign difluorocarbene precursor

Y Zafrani, G Sod-Moriah, Y Segall

Index: Zafrani, Yossi; Sod-Moriah, Gali; Segall, Yoffi Tetrahedron, 2009 , vol. 65, # 27 p. 5278 - 5283

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Citation Number: 40

Abstract

A convenient method for the difluoromethylation of phenols and thiophenols, using diethyl bromodifluoromethylphosphonate (1) as a difluorocarbene precursor, is described. This commercially available phosphonate was found to undergo an extremely facile P–C bond cleavage on basic hydrolysis (− 78° C to rt), presumably leading to the bromodifluoromethyl anion, which subsequently converts to a difluorocarbene intermediate. The latter is ...

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