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Org Lett. 2007 Sep 13;9(19):3797-800. Epub 2007 Aug 22.

An efficient, inexpensive, and shelf-stable diazotransfer reagent: imidazole-1-sulfonyl azide hydrochloride.

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1
Chemistry M313, School of Biomedical, Biomolecular & Chemical Sciences, The University of Western Australia, Crawley WA 6009, Australia. goddae01@student.uea.edu.au

Erratum in

  • Org Lett. 2011 May 6;13(9):2514.

Abstract

The design and synthesis of a new diazotransfer reagent, imidazole-1-sulfonyl azide hydrochloride, are reported. This reagent has proven to equal 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.

PMID:
17713918
DOI:
10.1021/ol701581g
[Indexed for MEDLINE]
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