Synthesis of Dibenzopyranones through Palladium‐Catalyzed Directed C–H Activation/Carbonylation of 2‐Arylphenols

Luo, Shuang; Luo, Fei‐Xian; Zhang, Xi‐Sha; Shi, Zhang‐Jie

doi:10.1002/anie.201304295

Cited by 158 publications

(38 citation statements)

References 59 publications

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“…A series of deuterium labeling experiments were conducted. Based on the results, they proposed that the C-H activation step might go through a S E Ar mechanism, and the C-H activation might be involved in the rate-determining step [112]. Later, Chuang and co-workers realized the same reaction under acid-base-free and mild conditions with Pd(OAc) 2 as the catalyst and AgOAc as oxidant (39b).…”

Section: Synthesis Of Six-membered Heterocycles Via Oxidative Carbonymentioning

confidence: 94%

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Xing

2015

Topics in Heterocyclic Chemistry

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With the assistance of a proper oxidant, carbonylation of two nucleophiles can take place directly in carbonylation conditions, which is defined as oxidative carbonylation. This process starts with the reaction of nucleophiles with the metal catalyst in oxidation state (M (n + 2) ), followed by insertion of CO and subsequent reductive elimination, providing the carbonylated products and the metal catalyst in reduction state (M (n) ). The oxidant could reoxidize M (n) to M (n + 2) to promote the catalytic cycle. Oxidative carbonylation avoids the difficult oxidative addition of R-X to metal catalyst, so this kind of carbonylation could proceed in mild conditions. What's more is that oxidative carbonylation doesn't need prefunctionalization of substrates. So, it's no wonder that considerable attention has been drawn to construct important carbonylated compounds through oxidative carbonylation. Particularly, much progress in synthesis of carbonylated heterocycles via oxidative carbonylation has been achieved in the past decades. Here, we summarized the main achievements in this area from 1982 to the beginning of 2015.

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Section: Synthesis Of Six-membered Heterocycles Via Oxidative Carbonymentioning

confidence: 94%

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Xing

2015

Topics in Heterocyclic Chemistry

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“…The demand for a longer reaction time than 24 h is likely due to the slow C-O reductive elimination process. 8a Our naïve thought to use bases as additives to quench the slightly acidic conditions, such as using NaOAc, KOAc and 2,4,6-collidine, did not improve the yields (entries [18][19][20]. Neither the explored reaction took place under more acidic conditions with extra acidic additives such as TFA or AcOH (entries 21 and 22).…”

mentioning

confidence: 99%

One pot synthesis of bioactive benzopyranones through palladium-catalyzed C–H activation and CO insertion into 2-arylphenols

et al. 2013

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“…Die Gruppe von Shi berichtete über eine ähnliche Carbonylierung von 2‐Arylphenolen, von der angenommen wird, dass sie eine elektrophile Cyclopalladierung am nichtphenolischen Ring umfasst . Kinetische Studien lassen darauf schließen, dass die C‐H‐Aktivierung über einen S E Ar‐ und nicht über einen CMD‐Mechanismus verläuft.…”

Section: Anellierungen Durch C‐h‐aktivierung Migratorische Insertiounclassified

Metallkatalysierte Anellierungen durch Aktivierung und Spaltung von C‐H‐Bindungen

2016

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Die außerordentliche Zunahme der Zahl katalytischer Umwandlungen über eine metallvermittelte Aktivierung von zuvor als inert angesehenen C‐H‐Bindungen zeugt von einem grundlegenden Wandel auf dem Gebiet der Synthesechemie. Während die meisten Reaktionen mit C‐H‐Aktivierung einfache Funktionalisierungen oder Additionen sind, wuchs in den letzten Jahren das Interesse an verwandten Umwandlungen, die formal als Cycloadditionsprozesse betrachtet werden können. Diese Reaktionen sind besonders für die Synthese vielversprechend, da sie die schnelle und nachhaltige Umwandlung leicht zugänglicher Substrate in wertvolle cyclische Produkte ermöglichen. In vielen Fällen entstehen bei diesen Anellierungsreaktionen metallacyclische Intermediate, die denen der herkömmlichen metallkatalysierten Cycloadditionen ungesättigter Vorstufen ähneln.

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Synthesis of Dibenzopyranones through Palladium‐Catalyzed Directed C–H Activation/Carbonylation of 2‐Arylphenols

Abstract: Dibenzopyranones were synthesized by a palladium-catalyzed phenol-directed C-H activation/carbonylation of 2-phenylphenol derivatives in the presence of CO. Pd(OAc)2 was used as a catalyst and Cu(OAc)2 as a catalytic oxidant in the presence of air.

Cited by 158 publications

References 59 publications

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

One pot synthesis of bioactive benzopyranones through palladium-catalyzed C–H activation and CO insertion into 2-arylphenols

Metallkatalysierte Anellierungen durch Aktivierung und Spaltung von C‐H‐Bindungen

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