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Synthesis 2012(1): 93-98  
DOI: 10.1055/s-0031-1289626
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Selective Protection and Deprotection of ortho-Functionalized Arylphosphonates

Elodie Lagadic, Yann Garcia, Jacqueline Marchand-Brynaert*
Université catholique de Louvain, Institute of Condensed Matter and Nanosciences (IMCN)- Molecules, Solids and Reactivity (MOST), Bâtiment Lavoisier, place Louis Pasteur, L4.01.02, 1348 Louvain-la-Neuve, Belgium
Fax: +32(10)474168; e-Mail: Jacqueline.Marchand@uclouvain.be;
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Publication History

Received 4 October 2011
Publication Date:
02 December 2011 (online)

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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

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