Synthesis 2002(17): 2473-2483
DOI: 10.1055/s-2002-35622
REVIEW
© Georg Thieme Verlag Stuttgart · New York

New Preparation of sp2 Organometallic Derivatives

Nicka Chinkov, Helena Chechik, Swapan Majumdar, Ilan Marek*, Annie Liard
Department of Chemistry and Institute of Catalysis Science and Technology, Technion-Israel Institute of Technology, Haifa 32000, Israel.
Fax: +972(4)8293709; e-Mail: chilanm@tx.technion.ac.il;
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Publikationsverlauf

Received 22 July 2002
Publikationsdatum:
20. November 2002 (online)

Abstract

Various polysubstituted, metalated olefins are easily prepared from heterosubstituted alkenes such as vinyl enol ethers, vinyl sulfides, sulfoxides and even sulfones in a one-step procedure. A complete isomerization was observed in this process, which leads only to the E isomer.

  • 1 Introduction

  • 1.1 Oxidative Metallation of Organic Halides

  • 1.2 Metal-Halogen Exchange

  • 1.3 Metal-Hydrogen Exchange

  • 1.4 Hydrometallation Reactions

  • 1.5 Carbometallation Reactions

  • 1.6 Transmetallation Reactions

  • 1.7 The Shapiro Reaction

  • 2 Limitations of these Methods

  • 3 Zirconocene Complexes in Organic Synthesis

  • 4 Discussion

  • 4.1 Vinylic Enol Ether into Vinylic Organometallic Derivatives

  • 4.1.1 Mechanistic Discussion

  • 4.2 Vinylic Thioenol Ether into Vinylic Organometallic Derivatives

  • 4.3 Vinyl Sulfoxides into Vinylic Organometallic Derivatives

  • 4.4 Vinyl Sulfones into Vinylic Organometallic Derivatives

  • 5 Conclusions