Synlett 2016; 27(07): 1096-1099
DOI: 10.1055/s-0035-1561558
letter
© Georg Thieme Verlag Stuttgart · New York

Metal-Mediated Debromination of gem-Dibromoalkenes under Mild Conditions

Raquel G. Soengas*
a   Department of Chemistry & QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Email: artur.silva@ua.pt   Email: rsoengas@ua.pt
,
Humberto Rodríguez-Solla
b   Department of Organic and Inorganic Chemistry, University of Oviedo, Julián Clavería, 7, 33071 Oviedo, Spain
,
Artur M. S. Silva*
a   Department of Chemistry & QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Email: artur.silva@ua.pt   Email: rsoengas@ua.pt
› Author Affiliations
Further Information

Publication History

Received: 21 November 2015

Accepted after revision: 30 December 2015

Publication Date:
20 January 2016 (online)


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Abstract

We describe the facile and efficient metal-promoted reduction of C–Br bonds of gem-dibromides. When the reaction is mediated by indium, the corresponding vinyl bromides are obtained in good yields and high E-stereoselectivities. Alternatively, when the reduction is mediated by samarium diiodide, vinyl bromides are obtained in moderate yields and good Z-selectivities.

Supporting Information