Alkynylboranes in the Suzuki-Miyaura coupling

Soderquist, John A.; Matos, Karl; Rane, Anil; Ramos, Jorge

doi:10.1016/0040-4039(95)00322-4

Cited by 109 publications

(36 citation statements)

References 8 publications

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“…242) which undergo the SM cross-coupling efficiently to produce various alkynyl derivatives (Scheme 113). 260 At approximately the same time, Fürstner and Seidel reported a similar type of SM cross-coupling reaction. 261 Colobert and co-workers later demonstrated the SM crosscoupling reaction to be an alternative to the Sonogashira coupling between the alkynylboronic ester 243 and aryl halides in quantitative yields (Scheme 114).…”

Section: Coupling Of Sp Hybridised C -B Compoundsmentioning

confidence: 90%

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,646

530

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Section: Coupling Of Sp Hybridised C -B Compoundsmentioning

confidence: 90%

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,646

530

View full text Add to dashboard Cite

“…[184] The palladium-catalyzed coupling of a number of preformed metal acetylides (e.g. Zn, [185] Mg, [186] B, [187] Al, [188] and Sn [189] derivatives) with organic electrophiles also provides a useful access to substituted alkynes. Nevertheless, the Sonogashira protocol (employing cocatalytic Cu I salts) is the most widely used of the palladium-catalyzed alkynylation methods, particularly in the context of total synthesis, largely owing to its broad applicability and convenience.…”

Section: The Sonogashira Reactionmentioning

confidence: 99%

Palladium‐Catalyzed Cross‐Coupling Reactions in Total Synthesis

2005

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In studying the evolution of organic chemistry and grasping its essence, one comes quickly to the conclusion that no other type of reaction plays as large a role in shaping this domain of science than carbon-carbon bond-forming reactions. The Grignard, Diels-Alder, and Wittig reactions are but three prominent examples of such processes, and are among those which have undeniably exercised decisive roles in the last century in the emergence of chemical synthesis as we know it today. In the last quarter of the 20th century, a new family of carbon-carbon bond-forming reactions based on transition-metal catalysts evolved as powerful tools in synthesis. Among them, the palladium-catalyzed cross-coupling reactions are the most prominent. In this Review, highlights of a number of selected syntheses are discussed. The examples chosen demonstrate the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.

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“…[184] Einen nützlichen Zugang zu substituierten Alkinen bietet zwar auch die palladiumkatalysierte Kupplung von vorab gebildeten Metallacetyliden (z. B. Zn-, [185] Mg-, [186] B-, [187] Al- [188] und Sn-Derivaten) [189] mit organischen Elektrophilen, dennoch ist das Sonogashira-Protokoll (mit Kupfer(i)-Salzen als Cokatalysatoren) wegen seiner großen Anwendungsbreite und bequemen Ausführbarkeit die am häufigsten verwendete palladiumkatalysierte Alkinylierungsmethode in der Totalsynthese.…”

Section: Aufsätzeunclassified

Palladiumkatalysierte Kreuzkupplungen in der Totalsynthese

2005

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Wenn man die Entwicklung der organischen Chemie betrachtet, kommt man schnell zu dem Schluss, dass kein Reaktionstyp dieses Gebiet in vergleichbarer Weise geprägt hat wie die Kohlenstoff‐Kohlenstoff‐Kupplungen. Grignard‐, Diels‐Alder‐ und Wittig‐Reaktionen sind nur drei herausragende Beispiele für solche Prozesse, die im vergangenen Jahrhundert zweifellos entscheidend am Aufstieg der chemischen Synthese beteiligt waren. Im letzten Viertel des 20. Jahrhunderts bereicherte eine neue Familie von leistungsfähigen Reaktionen zur Knüpfung von Kohlenstoff‐Kohlenstoff‐Bindungen das Repertoire der Synthesechemie: die übergangsmetallkatalysierten Reaktionen, allen voran die palladiumkatalysierten Kreuzkupplungen. In diesem Aufsatz werden Auszüge aus einer Reihe von ausgewählten Synthesen diskutiert. Die Beispiele sollen die enorme Leistungsfähigkeit dieser Prozesse in der Kunst der Totalsynthese aufzeigen und ihr Potenzial für zukünftige chemische Synthesen unterstreichen.

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Alkynylboranes in the Suzuki-Miyaura coupling

Cited by 109 publications

References 8 publications

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Palladium‐Catalyzed Cross‐Coupling Reactions in Total Synthesis

Palladiumkatalysierte Kreuzkupplungen in der Totalsynthese

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