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Synthesis 2009(19): 3311-3321  
DOI: 10.1055/s-0029-1216947
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Benzoate-Functionalized Phosphanes as Novel Building Blocks for the Traceless Staudinger Ligation

Constantin Mamat*a, Anke Flemmingb, Martin Köckerlingb, Jörg Steinbacha, Frank R. Wuestc
a Institut für Radiopharmazie, Forschungszentrum Dresden-Rossendorf e. V., Postfach: 50 01 19, 01314 Dresden, Germany
Fax: +49(351)2602915; e-Mail: c.mamat@fzd.de;
b Institut für Chemie, Universität Rostock, Albert-Einstein-Straße 3a, 18059 Rostock, Germany
c Department of Oncologic Imaging, Cross Cancer Institute, University of Alberta, Edmonton, AB, T6G 1Z2, Canada
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Publikationsverlauf

Received 2 March 2009
Publikationsdatum:
21. August 2009 (online)

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Abstract

A new synthetic pathway for the preparation of benzoate-functionalized phosphanes for microwave-mediated traceless Staudinger ligations is described. Novel phosphane derivatives based on 4-substituted iodophenyl benzoates were prepared via palladium(II)-catalyzed P-C cross-coupling reaction strategy in high yields. The application of microwave conditions for the ligation reactions reduced the reaction time considerably. An approach to fast and facile labeling strategies using this ligation was established.

Key words

Staudinger ligation - traceless - click chemistry - P-C cross-coupling - palladium-catalyzed

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17

CCDC 708661 (compound 4a), and 708662 (compound 10c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

29

Compound 5f was prepared according to the procedure given in reference 28 with 1-bromo-2-fluoroethane instead of 2-bromoethanol.