“On‐Water” Bisphosphorylation of β‐Trifluoromethyl Enones via Successive C(sp3)─F Bonds Functionalization: Synthesis of Multi‐Substituted Furans

A transition metal-free method for the bisphosphorylation of β-trifluoromethyl enones with phosphine oxides in pure water was developed for the synthesis of densely functionalized furan derivatives.

Abstract

The selective functionalization of C(sp³)─F bonds in accessible trifluoromethyl compounds is challenging but attractive. An “on-water” defluorinative bisphosphorylation of β-trifluoromethyl enones and phosphine oxides were developed for the modular synthesis of valuable multi-substituted furans. This reaction proceeded through the successive functionalization of the trifluoromethyl group on enones, enabling the construction of one O-heterocycle, the formation of three C─P/C─O bonds, and the cleavage of three C(sp³)─F bonds under transition metal-free reaction conditions. The aqueous solution also plays a unique role in determining the reaction reactivity and selectivity.

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