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Synlett 2010(5): 787-789  
DOI: 10.1055/s-0029-1219353
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Water-Soluble Phosphinophenol for Traceless Staudinger Ligation

Samuel H. Weisbrod, Andreas Marx*
Department of Chemistry and Konstanz Research School Chemical Biology, University of Konstanz, 78457 Konstanz, Germany
Fax: +49(7531)885140; e-Mail: andreas.marx@uni-konstanz.de;
Further Information

Publication History

Received 6 December 2009
Publication Date:
25 January 2010 (online)

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Abstract

The traceless Staudinger ligation can be mediated in ­water without organic co-solvents if charged groups render the phenylphosphine reagent water soluble. Here the synthesis of a new water-soluble phosphine is presented based on a diphenylphosphino­phenol reagent. Staudinger ligation with this reagent and azido glycine amide showed conversion of 77%.

Key words

amide - phenol - Staudinger ligation - conjugation - phosphine

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