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An Efficient, Inexpensive and Shelf-Stable Diazotransfer Reagent: Imidazole-1-sulfonyl Azide Hydrochloride

Ethan D. Goddard-Borger* and Robert V. Stick

*Chemistry M313, School of Biomedical, Biomolecular & Chemical Sciences, The University of Western Australia, Crawley WA 6009, Australia, Email: goddae01student.uwa.edu.au

E. D. Goddard-Borger, R. V. Stick, Org. Lett., 2007, 9, 3797-3800.

DOI: 10.1021/ol701581g (free Supporting Information)


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Abstract

Imidazole-1-sulfonyl azide hydrochloride equals triflyl azide in its ability to act as a “diazo donor” in the conversion of both primary amines into azides and activated methylene substrates into diazo compounds. Crucially, this reagent can be prepared in a one-pot reaction on a large scale from inexpensive materials, is shelf-stable and is conveniently crystalline.

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Key Words

Azides


ID: J54-Y2007-2980