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Zinc: Organometallic Chemistry

  1. Jean-Michel Grévy

Published Online: 15 MAR 2006

DOI: 10.1002/0470862106.ia261

Encyclopedia of Inorganic Chemistry

Encyclopedia of Inorganic Chemistry

How to Cite

Grévy, J.-M. 2006. Zinc: Organometallic Chemistry . Encyclopedia of Inorganic Chemistry. .

Author Information

  1. Universidad Autónoma del Estado de Morelos, Cuernavaca, México

Publication History

  1. Published Online: 15 MAR 2006

Abstract

Since the discovery of the first organozinc compounds by Sir Edward Frankland in 1849, the organometallic chemistry of zinc made remarkable advances and organozinc species have become essential tools for organic chemists. During the past decade, numerous new and modified procedures for the preparation of the title compounds have been published, rendering their synthesis easier, faster, and less expensive and giving higher yields. The coordination chemistry of organozinc derivatives has been subject of further interest and various intra- and intermolecular complexes with different donor ligands have been structurally characterized by X-ray crystallography and spectroscopic methods. The accumulation of molecular structures, physicochemical studies, and computational calculations has led to a better understanding of the organozinc chemistry, and consequently to the design of new derivatives for specific applications. Even if the development of areas like the chemistry of organozinc anions and cations is still in its early stage, these compounds, which exhibit properties different than those of the parent organometallic species, appear to have promising applications in synthesis and catalytic reactions. During the past ten years, the chemistry of organo-gem-dizincio derivatives has also been the subject of much interest and progress. These reagents can form two carbon–carbon bonds in a one-pot reaction and with high stereoselectivity. They became key reagents for organic chemists who want to combine multiple transformations in one operation. The importance of organometallic compounds of zinc can be seen in the growing number of their applications in synthesis. They are used in many reactions such as substitutions, additions to carbonyl compounds and unsaturated systems, cyclopropanations, and polymerizations. Furthermore, as a result of their low reactivity, they tolerate a wide variety of functionalities and perform most of the transformations with high regio- and enantioselectivity. After spending more than half a century in the shade of Grignard and organolithium reagents, organozinc reagents are becoming more and more important in modern chemistry.

Keywords:

  • organozinc;
  • coordination;
  • anion;
  • cation;
  • organo-gem-dimetallic;
  • regioselective-addition;
  • diastereoselectivity;
  • enantioselectivity;
  • carbenoid;
  • Reformatsky;
  • polymerization;
  • Simmons–Smith