Cu-catalyzed debrominative cyanation of gem-dibromoolefins: a facile access to α,β-unsaturated nitriles?

Organic & Biomolecular Chemistry Pub Date: 2015-04-20 DOI: 10.1039/C5OB00394F

Abstract

An efficient catalytic route for the synthesis of α,β-unsaturated nitriles from easily accessible gem-dibromoolefins has been developed. The method utilized inexpensive reagents such as Cu2O as a catalyst, L-proline as a ligand and NaCN as a cyanide source to afford α,β-unsaturated nitriles in high yields (62–86%). A deuterium exchange study has shown that one of the bromide atoms of gem-dibromoolefins exchanges with cyanide while the other with a deuterium atom.

Graphical abstract: Cu-catalyzed debrominative cyanation of gem-dibromoolefins: a facile access to α,β-unsaturated nitriles
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