Diethyl acetylphosphonate

CAS 919-19-7, Cat. No EN300-257056
Reagent acyl-anion equivalent

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Diethyl acetylphosphonate is a reagent that functions as a masked acyl-anion equivalent under N-heterocyclic carbene (NHC) catalysis. It serves as the key substrate enabling the tandem [1,2]-phospha-Brook/[1,4]-phosphate rearrangement, a transformation that converts aldehydes into α-ketophosphates in high yields¹. The methodology shows a broad scope of substrates, reacting efficiently with electron-rich and electron-poor aromatic aldehydes as well as challenging aliphatic aldehydes. The process is cyanide-free, mild, and highly chemoselective, offering a practical route to synthetically valuable α-ketophosphates. Overall, diethyl acetylphosphonate is a stable, versatile, and highly effective acyl phosphonate reagent, uniquely suited for NHC-driven acyl-anion chemistry and tandem rearrangement processes.

Synonyms: O,O-diethyl acetylphosphonate; 1-diethoxyphosphorylethanone; 1-(diethoxyphosphinyl)ethenone; diethyl (1-oxoethyl)phosphonate; acetylphosphonic acid diethyl ester