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Barbier Reaction

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr047

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Barbier Reaction. Comprehensive Organic Name Reactions and Reagents. 47:202–209.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

In the Barbier reaction, both alkyl halides and carbonyl compounds are simultaneously mixed with magnesium turnings and form carbon-carbon bonds in one-step. It has been reported that small excess of the toxic halide can be used, and similar results, including the R:S ratio, with respect to the Grignard reaction can be obtained. This reaction is known to be preferable for halides and is believed to go through the single-electron transfer (SET) process. Presently, many zero-valent metals have been successfully applied to similar reaction conditions. It has been reported that nonpolar solvents favor R-regioselection whereas polar solvents lead to γ-syn selection. This reaction has wide applications in organic synthesis.

Keywords:

  • Grignard reagents;
  • single-electron transfer (SET);
  • R-regioselection;
  • γ-syn selection