Abstract

There has been rapid progress and growing interest in alkyne metathesis within the past decade. The availability of highly active catalysts as well as their applications in both organic synthesis and polymer chemistry has served to motivate the advancement of this field. In this article, the development of several different metathesis catalysts, including two heterogeneous ones, are reviewed with an emphasis on comparing strengths and weaknesses. In Section 4, the applications of alkyne metathesis to synthesis of natural products, conjugated polymers as well as shape-persistent macrocycles are discussed. In the last section, a comparison of alkyne metathesis to the well established alkene metathesis is given. Developing an alkyne metathesis catalyst with both high reactivity and robustness to air and moisture remains an unsolved problem of this important and useful reaction. 1 Introduction 2 Mechanistic Overview 3 Catalyst Synthesis 3.1 Homogeneous Systems 3.2 Heterogeneous Systems 4 Synthetic Applications of Alkyne Metathesis 4.1 Ring-Closing Alkyne Metathesis (RCAM) 4.2 Natural Product Synthesis 4.3 Polymer Synthesis 4.4 Cyclooligomerization 5 Alkyne Metathesis vs. Alkene Metathesis 5.1 Catalysts 5.2 Cross-Metathesis 5.3 Ring-Opening Metathesis 5.4 Ring-Closing Metathesis 5.5 Cyclooligomerization 5.6 Acyclic Diene/Diyne Metathesis 6 Conclusion and Outlook

Original languageEnglish (US)
Pages (from-to)93-120
Number of pages28
JournalAdvanced Synthesis and Catalysis
Volume349
Issue number1-2
DOIs
StatePublished - Jan 1 2007

Fingerprint

Alkynes
Catalysts
Olefins
Alkenes
Biological Products
Polymers
Conjugated polymers
Moisture
Availability
Air

Keywords

  • Acyclic diyne synthesis
  • Cyclooligomerization
  • Metathesis
  • Poly(arylene-ethynylene)s
  • Ring-closing alkyne metathesis
  • Shape-persistent macrocycles

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Organic Chemistry
  • Catalysis

Cite this

Alkyne metathesis : Catalysts and synthetic applications. / Zhang, Wei; Moore, Jeffrey S.

In: Advanced Synthesis and Catalysis, Vol. 349, No. 1-2, 01.01.2007, p. 93-120.

Research output: Contribution to journalReview article

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