New preparation of sp2 organometallic derivatives

Nicka Chinkov, Helena Chechik, Swapan Majumdar, Ilan Marek, Annie Liard

Research output: Contribution to journalReview articlepeer-review

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.

Original languageEnglish
Pages (from-to)2473-2483
Number of pages11
JournalSynthesis
Issue number17
DOIs
StatePublished - 2002
Externally publishedYes

Keywords

  • Stereoselectivity
  • Vinyl enol ethers
  • Vinyl sulfides
  • Vinyl sulfones
  • Vinyl sulfoxides
  • Zirconocene complexes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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