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Amberlite IRA900N₃ as a New Catalyst for the Azidation of α,β-Unsaturated Ketones under Solvent-Free Conditions

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Luca Castrica, Francesco Fringuelli,* Luisa Gregoli, Ferdinando Pizzo, and Luigi Vaccaro*

CEMINDipartimento di Chimica, Universit di Perugia, Via Elce di Sotto, 8, I-06123 Perugia, Italy luigi@unipg.it; frifra@unipg.it

J. Org. Chem., 2006, 71 (25), pp 9536–9539

DOI: 10.1021/jo061791b

Publication Date (Web): November 15, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Amberlite IRA900N₃ is an excellent organocatalyst for the azidation of α,β-unsaturated ketones with trimethylsilyl azide under solvent-free conditions. By avoiding the use of metallic species and of the organic reaction medium, the procedure is a green tool for the preparation of β-azido ketones under mild conditions with yields from good to excellent. The catalyst can be recovered and re-used with no loss of its efficiency.

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Published In Issue December 08, 2006
Received August 30, 2006

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Amberlite IRA900N₃ as a New Catalyst for the Azidation of α,β-Unsaturated Ketones under Solvent-Free Conditions