Functionalized aromatic alkylphosphonates, hemi-phosphonates
and phosphonic acids are good candidates to elaborate water-soluble
building blocks. The key step of the synthesis developed here consisted
of the introduction of a phosphoryl group by an ortho-metallation
reaction from protected ortho-anisidine.
A practical route to phosphonated benzoxazoles was thus discovered. Chemoselective
deprotections were investigated and mono-, bis-, and ter-deprotected
aromatic derivatives were obtained.
chemoselectivity - cleavage - heterocycles - deprotection - aromatic phosphonates
