Reaction of Azides with Dichloroindium Hydride:  Very Mild Production of Amines and Pyrrolidin-2-imines through Possible Indium−Aminyl Radicals

Luisa Benati, Giorgio Bencivenni,* Rino Leardini, Daniele Nanni,* Matteo Minozzi, Piero Spagnolo, Rosanna Scialpi, and Giuseppe Zanardi
Dipartimento di Chimica Organica A. Mangini, Universit di Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy
Org. Lett., 2006, 8 (12), pp 2499–2502
DOI: 10.1021/ol0606637
Publication Date (Web): May 16, 2006
Copyright © 2006 American Chemical Society
*

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

, nanni@ms.fci.unibo.it

Abstract

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Organic azides are easily reduced to the corresponding amines by reaction with dichloroindium hydride under very mild conditions and in a highly chemoselective fashion. γ-Azidonitriles give rise to outstanding five-membered cyclizations affording pyrrolidin-2-imines. A rationalization of the overall experimental data cannot exclude the occurrence of competitive radical and nonradical pathways, but certain results are, however, soundly consistent with the intermediacy of indium-bound nitrogen-centered radicals.

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History

  • Published In Issue June 08, 2006
  • Received March 17, 2006

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