6-Halopurines in palladium-catalyzed coupling with organotin and organozinc reagents

Gundersen, Lise‐Lotte; Bakkestuen, Anne Kristin; Aasen, Arne Jørgen; Øver»s, Herald; Rise, Frode

doi:10.1016/s0040-4020(01)85540-x

Cited by 91 publications

(33 citation statements)

References 35 publications

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“…As with Suzuki and Stille couplings, there are quite a few examples of heteroaryl chlorides, mainly nitrogen‐containing species, which participate in the Negishi reaction. Thus, chloropyridines,141 pyrazines,15a, 142 pyrimidines,143 and triazines144 are suitable substrates, as are fused heterocycles such as chloroquinolines,18b, 110d, 145 quinazolines,113 and purines 25d, 116b…”

Section: Carbon–carbon Bond‐forming Reactionsmentioning

confidence: 99%

Palladium-Catalyzed Coupling Reactions of Aryl Chlorides

Littke

2002

Angew. Chem. Int. Ed.

2,714

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: 99%

Palladium-Catalyzed Coupling Reactions of Aryl Chlorides

Littke

2002

Angew. Chem. Int. Ed.

2,714

1,214

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“…Wie bei den Suzuki‐ und Stille‐Kupplungen gibt es nur wenige Heteroarylchloride, hauptsächlich stickstoffhaltige Verbindungen, die die Negishi‐Kupplung eingehen. So sind Chlorpyridine,141 Pyrazine,15a, 142 Pyrimidine143 und Triazine144 geeignete Substrate, ebenso kondensierte Heterocyclen wie Chlorchinoline,18b, 110d, 145 Chinazoline113 und Purine 25d, 116b…”

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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“…Unfortunately rearrangement of the isomer 9a was not successful, here only reductive removal of the chloride was observed (data not shown). We have also previously observed (in Negishi couplings) that 7‐substituted‐6‐chloropurines are more prone to reduction compared to their 9‐substituted isomers 22…”

Section: Resultsmentioning

confidence: 59%

Synthesis of N‐Alkenylpurines by Rearrangements of the Corresponding N‐Allyl Isomers: Scopes and Limitations

Kania

Gundersen

2013

Eur J Org Chem

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N‐9‐ and N‐7‐alkenylpurines have been synthesized by rearrangement of the corresponding N‐allyl derivatives, often in good yields and with high stereoselectivity. Base promoted and transition metal mediated rearrangements have been studied. Simple allylpurines were easily rearranged with catalytic amounts of RuClH(CO)(PPh3)3. The efficiency of base promoted rearrangement was highly dependent on the detailed structure of the starting material, but this reaction often occurred with surprisingly high Z‐selectivity.

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6-Halopurines in palladium-catalyzed coupling with organotin and organozinc reagents

Cited by 91 publications

References 35 publications

Palladium-Catalyzed Coupling Reactions of Aryl Chlorides

Palladium-Catalyzed Coupling Reactions of Aryl Chlorides

Palladiumkatalysierte Kupplungen von Arylchloriden

Synthesis of N‐Alkenylpurines by Rearrangements of the Corresponding N‐Allyl Isomers: Scopes and Limitations

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