Electrochemically Oxidative Phosphating of Aldehydes and Ketones

Abstract

Disclosed herein is the first protocol for the electrochemically oxidative phosphating of aldehydes and ketones to generate α-hydroxyphosphine oxides with diphenylphosphine as the phosphine source. Various phosphating products containing P–C bonds are basically assembled in modest to excellent yields. This electrochemical phosphating was achieved by utilizing a simple undivided cell with foam nickel electrodes at room temperature without the addition of any oxidant or metal catalyst. The prepared α-hydroxyphosphine oxides possess potential application in pharmacological research.

C- and N-Phosphorylated Enamines—An Avenue to Heterocycles: NMR Spectroscopy

“…The transformation of compounds 63-67 under the action of SO2 into 1,4-azaphosphorines (68)(69)(70)(71)(72) occurs much more slowly than similar transformations of acyclic alkenyltrichlorophosphonium hexachlorophosphonates. The transformation of compounds 63-67 under the action of SO 2 into 1,4-azaphosphorines (68-72) occurs much more slowly than similar transformations of acyclic alkenyltrichlorophosphonium hexachlorophosphonates.…”

“…Organophosphorus compounds obtained by phosphorylation of urea derivatives and related compounds are widely used in the life sciences, medicine chemistry, pharmaceuticals, organic catalysis and materials science [63][64][65][66][67][68][69][70][71][72]. Efficient P-C or P-N bond formation using the various available phosphorus sources plays a critical role in the construction of organophosphorus compounds.…”

“…Scheme 15. The formation of hexachlorophosphorates of 1,4-azaphosphoniarines (63-67) and 1,4-azaphosphorines(68)(69)(70)(71)(72).…”