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  Alkyne Metathesis in Organic Synthesis

Fürstner, A. (2015). Alkyne Metathesis in Organic Synthesis. In B. M. Trost, & C.-J. Li (Eds.), Modern Alkyne Chemistry: Catalytic and Atom-Economic Transformations (pp. 69-111). Weinheim: Wiley-VCH. doi:10.1002/9783527677894.ch4.

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Datensatz-Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-659A-5 Versions-Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-6878-8
Genre: Buchkapitel

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 Urheber:
Fürstner, Alois1, Autor           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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Schlagwörter: alkyne metathesis catalysts; cyclo-oligomerization; molybdenum alkylidyne; organic synthesis
 Zusammenfassung: This chapter illustrates the scope and limitations of alkyne metathesis, which has become a powerful tool of contemporary organic synthesis. It begins with a discussion on classical catalyst systems and state-of-the-art catalysts. The generally accepted mechanism of alkyne metathesis, originally proposed by Katz and McGinnis, follows the logic of the Chauvin cycle of olefin metathesis. It consists of a sequence of - a priori - reversible [2 + 2] cycloaddition and cycloreversion steps. To render the reaction preparatively meaningful, the resulting equilibrium needs to be constantly perturbed by removing one of the products from the mixture. Limitations are encountered when working with very bulky substrates or with alkyne derivatives that display protic functionality able to exchange with the silanolate ligands that guarantee the outstanding performance of the operative molybdenum alkylidyne. An interesting reaction format is the cyclo-oligomerization of substrates containing two or more acetylene moieties in an appropriate spatial orientation.

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Sprache(n): eng - English
 Datum: 2014-10-102015
 Publikationsstatus: Erschienen
 Seiten: 43
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Expertenbegutachtung
 Identifikatoren: DOI: 10.1002/9783527677894.ch4
 Art des Abschluß: -

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Titel: Modern Alkyne Chemistry: Catalytic and Atom-Economic Transformations
Genre der Quelle: Buch
 Urheber:
Trost, Barry M.1, Herausgeber
Li, Chao-Jun2, Herausgeber
Affiliations:
1 Stanford University, Department of Chemistry, 330 Roth Way, Stanford, CA 94305-5080, USA, ou_persistent22            
2 McGill University, Department of Chemistry, 801 Sherbrook Street West, Montreal, Quebec H3A 0B8, Canada, ou_persistent22            
Ort, Verlag, Ausgabe: Weinheim : Wiley-VCH
Seiten: 43 Band / Heft: - Artikelnummer: - Start- / Endseite: 69 - 111 Identifikator: ISBN: 978-3-527-33505-3