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DOI: 10.1055/sos-SD-021-00911

Whitehead, A.; Sieck, S. R.; Mukherjee, S.; Hanson, P. R.Science of Synthesis, (200521908.

While Swern and analogous oxidations are known to be viable nonmetal routes to acylphosphonates,[‌5‌‌7‌] alternative routes have been reported. Alkylation of (dialkoxyphosphoryl)dithianes such as 3 under basic conditions provides substituted masked oxo phosphonates 4 (Scheme 2).[‌8‌] Hydrolysis of the dithioketals 4 with bromine and silver nitrate in aqueous acetonitrile gives an array of acylphosphonates 5 in good yield. This method provides a mild, nonthermal alternative to metal-promoted oxidations (see Section allowing for broad functional group compatibility.

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