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Reformatsky Reaction

(Reformatskii Reaction, Reformatsky Condensation)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr523

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Reformatsky Reaction. Comprehensive Organic Name Reactions and Reagents. 523:2314–2321.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The zinc-mediated formation of β-hydroxy esters from the condensation between α-bromoester and an aldehyde or ketone, or more generally the reaction between an activated alkyl halide with a carbonyl compound in the presence of zinc to form a hydroxy compound is generally known as the Reformatsky reaction, or Reformatskii reaction. The traditional Reformatsky protocol consists several drawbacks. The study finds that the use of an excess amount of zinc and α-bromoester can improve the yields. Small variation in the alcoholic moiety of α-bromoester affects the reactivity of the α-bromoester. In addition, many variants of α-bromoesters have been developed or used successfully for this reaction. This reaction has very broad applications in organic synthesis.

Keywords:

  • C-metalated species;
  • methyl γ-bromocrotonate;
  • β-amino esters;
  • β-hydroxy esters