Synlett 2014; 25(11): 1561-1564
DOI: 10.1055/s-0033-1339030
letter
© Georg Thieme Verlag Stuttgart · New York

Indium-Mediated Debromination of gem-Bromonitroalkanes under Mild Conditions in Aqueous Medium

Rita C. Acúrcio
Department of Chemistry & QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Fax: +351(234)370084   Email: artur.silva@ua.pt   Email: rsoengas@ua.pt
,
Raquel G. Soengas*
Department of Chemistry & QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Fax: +351(234)370084   Email: artur.silva@ua.pt   Email: rsoengas@ua.pt
,
Artur M. S. Silva*
Department of Chemistry & QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Fax: +351(234)370084   Email: artur.silva@ua.pt   Email: rsoengas@ua.pt
› Author Affiliations
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Publication History

Received: 15 March 2014

Accepted after revision: 08 April 2014

Publication Date:
13 May 2014 (online)


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Abstract

gem-Bromonitroalkanes are efficiently reduced into the corresponding dehalogenated products in excellent yields with indium metal in the presence of a palladium(0) catalyst and indium(III) chloride in aqueous medium. The addition of bromonitromethane to carbohydrate-derived aldehydes or imines, followed by debromination of the intermediate bromonitro compounds represents an extremely efficient method for the stereoselective preparation of nitrosugars.

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