Et4NCl-Promoted Electrochemical Atherton-Todd Type Reaction to Construct P(O)-F Bonds

Anelectrochemical synthetic strategy to construct P-(O)-Fbonds was developed via the Atherton-Todd reaction. Promotedby Et4NCl, a series of biologically active phosphoric fluorideswere synthesized by use of commercially available P-(O)-H feedstocksand Et3N center dot 3HF as the F-source. With this protocol,some potentially functional P-(O)-OR and P-(O)-SR motifscould also be smoothly forged. This sustainable fluorination approachfeatures step-economy, is chemical-oxidant- and metal-catalyst-free,and offers low cost and mild conditions. Additionally, cyclic voltammetryand control experiments were conducted to propose a reasonable mechanism.

Automated summary

An electrochemical synthetic strategy for constructing P-(O)-F bonds was developed through the Atherton-Todd reaction. With the promotion of Et4NCl, a series of biologically active phosphoric fluorides were synthesized using commercially available P-(O)-H feedstocks and Et3N center dot 3HF as the F-source. This sustainable fluorination approach features step-economy, is chemical-oxidant- and metal-catalyst-free, and offers low cost and mild conditions. Additionally, cyclic voltammetry and control experiments were conducted to propose a reasonable mechanism.