Palladium-Catalyzed Cross-Coupling Reaction of Haloazoles with Phenylsulfonylacetonitrile

Sakamoto, Takao; Kondo, Yoshinori; Suginome, Takashi; Ohba, Setsuya; Yamanaka, Hiroshi

doi:10.1055/s-1992-26163

Cited by 22 publications

(9 citation statements)

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“…The first example of a palladium‐catalyzed arylation of a stabilized carbanion by a heteroaryl or aryl chloride was provided by Yamanaka and co‐workers, who showed that diphenyl‐substituted 2‐chlorooxazoles and thiazoles can be coupled with phenylsulfonylacetonitrile in the presence of NaH [Eq. (44)] 188. The analogous 2‐chloro‐1‐methylimidazole is unreactive under these conditions.…”

Section: Carbon–carbon Bond‐forming Reactionsmentioning

confidence: 98%

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Palladium-Catalyzed Coupling Reactions of Aryl Chlorides

Littke

2002

Angew. Chem. Int. Ed.

2,694

1,214

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Collectively, palladium-catalyzed coupling reactions represent some of the most powerful and versatile tools available to synthetic organic chemists. Their widespread popularity stems in part from the fact that they are generally tolerant to a large number of functional groups, which allows them to be employed in a wide range of applications. However, for many years a major limitation of palladium-catalyzed coupling processes has been the poor reactivity of aryl chlorides, which from the standpoints of cost and availability are more attractive substrates than the corresponding bromides, iodides, and triflates. Traditional palladium/triarylphosphane catalysts are only effective for the coupling of certain activated aryl chlorides (for example, heteroaryl chlorides and substrates that bear electron-withdrawing groups), but not for aryl chlorides in general. Since 1998, major advances have been described by a number of research groups addressing this challenge; catalysts based on bulky, electron-rich phosphanes and carbenes have proved to be particularly mild and versatile. This review summarizes both the seminal early work and the exciting recent developments in the area of palladium-catalyzed couplings of aryl chlorides.

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Section: Carbon–carbon Bond‐forming Reactionsmentioning

confidence: 98%

“…(44)]. [188] The analogous 2-chloro-1-methylimidazole is unreactive under these conditions. The palladium-catalyzed a-arylation of a ketone with an aryl chloride was first reported by Buchwald and co-workers in which they used biphenyl ligand 1 [Eq.…”

Section: A-arylation Reactions Of Enolates and Other Stabilized Carbanionsmentioning

confidence: 99%

Palladium-Catalyzed Coupling Reactions of Aryl Chlorides

Littke

2002

Angew. Chem. Int. Ed.

2,694

1,214

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“…Diphenylsubstituierte 2‐Chloroxazole und ‐thiazole wurden mit Phenylsulfonylacetonitril in Gegenwart von NaH gekuppelt [Gl. (44)] 188. Das analoge 2‐Chlor‐1‐methylimidazol ist unter diesen Bedingungen nicht reaktiv.…”

Section: Reaktionen Zur Knüpfung Von Kohlenstoff‐kohlenstoff‐binduunclassified

Palladiumkatalysierte Kupplungen von Arylchloriden

2002

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Palladiumkatalysierte Kupplungen gehören zu den leistungsfähigsten und vielseitigsten Reaktionen, die dem organischen Chemiker für die Synthese zur Verfügung stehen. Ihre große Beliebtheit rührt teilweise daher, dass sie bei den Umsetzungen gewöhnlich viele funktionelle Gruppen tolerieren, was ihre breite Verwendung in vielen Bereichen ermöglicht. Allerdings unterlagen die palladiumkatalysierten Kupplungen jahrelang großen Einschränkungen durch die geringe Reaktivität der Arylchloride; diese Verbindungen sind in Bezug auf Kosten und Verfügbarkeit attraktivere Substrate als die entsprechenden Bromide, Iodide und Triflate. Herkömmliche Palladium/Triarylphosphan‐Katalysatoren setzten nur bestimmte aktivierte Arylchloride um (z. B. Heteroarylchloride und Substrate mit elektronenanziehenden Gruppen), nicht aber Arylchloride generell. Seit 1998 haben mehrere Forschungsgruppen bedeutende Fortschritte hinsichtlich dieser Herausforderung beschrieben; Katalysatoren mit voluminösen, elektronenreichen Phosphanen und Carbenen erwiesen sich als sehr vielseitig und ermöglichen besonders milde Reaktionsbedingungen. Dieser Aufsatz fasst die frühen, wegweisenden Arbeiten und die spannenden neuartigen Entwicklungen auf dem Gebiet der palladiumkatalysierten Kupplungen von Arylchloriden zusammen.

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“…90 Azole adducts 96 exist as mixtures of the aromatic azole and the conjugated enamine. Dimerization of bromothiazole (Scheme 42), 91 palladium and formation of 97 was isolated in an improved yield (86% vs. 62%).…”

Section: Heck and Ullmann Couplingsmentioning

confidence: 99%