Direct arylation of azine N-oxides with aryl triflates

Schipper, Derek J.; El-Salfiti, Mohamed; Whipp, Christopher J.; Fagnou, Keith

doi:10.1016/j.tet.2009.03.077

Cited by 99 publications

(46 citation statements)

References 39 publications

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“…[3] Recent work has shown that such reactions are applicable to activated pyridinium species. [4] In contrast, comparatively little has been published on direct alkenylation reactions; in particular, there are few examples of direct vinylations on activated pyridines. In these cases, symmetrical alkynes with little functionality or relatively simple Heck acceptors were required as the coupling partners.…”

Section: In Memory Of Keith Fagnoumentioning

confidence: 99%

Copper‐Catalyzed Direct Alkenylation of N‐Iminopyridinium Ylides

2010

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Section: In Memory Of Keith Fagnoumentioning

confidence: 99%

Copper‐Catalyzed Direct Alkenylation of N‐Iminopyridinium Ylides

2010

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“…Die effiziente direkte Arylierung einer Vielzahl von elektronenreichen Azolen gelang mit Aryliodiden, -triflaten [141] und -bromiden als Elektrophilen. [142] Insbesondere erwiesen sich Benzoxazole als ausgezeichnete Substrate für die palladiumkatalysierte direkte Arylierung, die selektiv an der C2-Position verlief (Schema 70).…”

Section: Angewandte Chemieunclassified

Übergangsmetallkatalysierte direkte Arylierungen von (Hetero)Arenen durch C‐H‐Bindungsbruch

2009

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Das Gebiet der übergangsmetallkatalysierten direkten Arylierung unter C‐H‐Bindungsbruch hat in den letzten Jahren eine rasante Entwicklung erfahren, was dazu führte, dass sich solche Methoden immer mehr als Alternativen zu den herkömmlichen Kreuzkupplungen mit metallorganischen Reagentien etabliert haben. Insbesondere wurden zahlreiche Palladium‐ und Rutheniumkatalysatoren beschrieben, welche die direkte Arylierung von (Hetero)arenen mit anspruchsvollen Reaktionspartnern ermöglichen; hierzu gehören elektrophile Arylchloride und ‐tosylate oder auch einfache Arene in gekreuzten dehydrierenden Arylierungen.

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“…Fagnou et al reported palladium-catalyzed direct arylation of pyridine N-oxides using aryl triflates to afford the corresponding 2-aryl pyridine N-oxides (Scheme 7). 14 …”

Section: Methodsmentioning

confidence: 99%

Synthesis of 2-substituted pyridines from pyridine N-oxides

Liu¹,

Luo²,

Xu³

et al. 2013

Arkivoc

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The synthesis of substituted pyridines has drawn the attention of many chemists due to their importance as building blocks for biologically active compounds and materials. This mini-review focuses on recent developments relating to the synthesis of substituted pyridines from pyridine N-oxides, along with their interesting mechanism aspects. New developments including alkenylation, alkynylation, alkylation, arylation, amination and cyanation are discussed.

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Direct arylation of azine N-oxides with aryl triflates

Cited by 99 publications

References 39 publications

Copper‐Catalyzed Direct Alkenylation of N‐Iminopyridinium Ylides

Copper‐Catalyzed Direct Alkenylation of N‐Iminopyridinium Ylides

Übergangsmetallkatalysierte direkte Arylierungen von (Hetero)Arenen durch C‐H‐Bindungsbruch

Synthesis of 2-substituted pyridines from pyridine N-oxides

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