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Journal ArticleDOI

Olefin Metathesis and Beyond

Alois Fürstner
- 01 Sep 2000 - 
- Vol. 39, Iss: 17, pp 3012-3043
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TLDR
In this paper, the authors provide an overview of the development of catalysts for olefin metathesis which combine high activity, durability, and excellent tolerance towards polar functional groups.
Abstract
The advent of well-defined catalysts for olefin metathesis which combine high activity, durability, and excellent tolerance towards polar functional groups has revolutionized the field. The past decade has seen the rapid embrace of these reagents as tools for advanced organic and polymer chemistry and the success of this development is witnessed by a plethora of elegant applications to the synthesis of natural and nonnatural products. This review article provides an overview of these developments and intends to familiarize the reader with some very recent advances which hold the promise to expand the scope of the reaction even further. Moreover, the positive impact of metathesis on the fundamental logic of retrosynthetic planning is demonstrated by means of typical examples. Finally, it will be shown that metathesis is by no means restricted to alkenes as substrates, and some comments on metathesis reactions following unconventional mechanistic pathways will also be presented.

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Citations
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N-heterocyclic carbenes: a new concept in organometallic catalysis.

TL;DR: N-Heterocyclic carbenes have become universal ligands in organometallic and inorganic coordination chemistry as mentioned in this paper, and they not only bind to any transition metal, be it in low or high oxidation states, but also to main group elements such as beryllium, sulfur, and iodine.
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Controlled microwave heating in modern organic synthesis.

TL;DR: This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.
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Heterocyclic Carbenes: Synthesis and Coordination Chemistry

TL;DR: New methods for the synthesis of complexes with N-heterocyclic carbene ligands such as the oxidative addition or the metal atom template controlled cyclized isocyanides have been developed recently.
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Dynamic covalent chemistry.

TL;DR: Some recent examples where dynamic covalent chemistry has been demonstrated are shown to emphasise the basic concepts of this area of science.
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Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts.

TL;DR: The fascinating story of olefin (or alkene) metathesis began almost five decades ago, when Anderson and Merckling reported the first carbon-carbon double-bond rearrangement reaction in the titanium-catalyzed polymerization of norbornene.
References
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Journal ArticleDOI

Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

TL;DR: These air- and water-tolerant complexes were shown to exhibit an increased ring-closing metathesis activity at elevated temperature when compared to that of the parent complex 2 and the previously developed complex 3.
Journal ArticleDOI

Synthesis and Applications of RuCl2(CHR‘)(PR3)2: The Influence of the Alkylidene Moiety on Metathesis Activity

TL;DR: In this paper, the reactions of RuCl2(PPh3)3 with a number of diazoalkanes were surveyed, and alkylidene transfer was observed for RCHN2 and various para-substituted aryl diazalkanes p-C6H4X CHN2.
Journal ArticleDOI

Recent advances in olefin metathesis and its application in organic synthesis

TL;DR: In this paper, a review of recent advances in olefin metathesis focusing on the areas of ring-closing olefi cation (RCM) and cross-metathesis is presented.
Book

Principles and applications of organotransition metal chemistry

TL;DR: A perspective survey of organotransition metal complexes according to ligand substitution processes can be found in this paper, with a focus on transition metal complexes with metal carbon-bonded ligands.
Journal ArticleDOI

Synthesis of molybdenum imido alkylidene complexes and some reactions involving acyclic olefins

TL;DR: In this paper, a precursor to imido alkylidene complexes that is related to 2 has been prepared by the sequence MoO{sub 2} {yields} MoO(NAr)Cl{sub 3} (dme = 1,2-dimethoxyethane) and Me{ sub 3}SiNHAr (Ar = 2,6-diisopropylphenyl) yields Mo(C-t-Bu)(NHAr), which upon treatment with a catalytic amount of NEt-sub 3] is transformed into
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