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Synthesis 2012(1): 93-98
DOI: 10.1055/s-0031-1289626
DOI: 10.1055/s-0031-1289626
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Selective Protection and Deprotection of ortho-Functionalized Arylphosphonates
Further Information
Publication History
Received
4 October 2011
Publication Date:
02 December 2011 (online)
Abstract
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.
Key words
chemoselectivity - cleavage - heterocycles - deprotection - aromatic phosphonates