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Catalytic Staudinger-Vilarrasa Reaction for the Direct Ligation of Carboxylic Acids and Azides

Jordi Burés, Manuel Martín, Félix Urpí and Jaume Vilarrasa*

*Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, 08028 Barcelona, Catalonia, Spain, Email: jvilarrasaub.edu

J. Burés, M. Martín, F. Urpí, J. Vilarrasa, J. Org. Chem., 2009, 74, 2203-2206.

DOI: 10.1021/jo802825e (free Supporting Information)


Abstract

2,2′-Dipyridyl diselenide catalyzes a direct reaction of carboxylic acids with azides and trimethylphosphine at room temperature. The mechanism of the process, which is not an aza-Wittig reaction, has been elucidated.


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proposed mechanism



Key Words

amides, Staudinger reaction, trimethylphosphine


ID: J42-Y2009-0820