From Anilines to Isatins: Oxidative Palladium‐Catalyzed Double Carbonylation of CH Bonds

Li, Wu; Duan, Zhengli; Zhang, Xueye; Zhang, Heng; Wang, Mengfan; Jiang, Ru; Zeng, Hongyao; Liu, Chao; Lei, Aiwen

doi:10.1002/anie.201410321

Cited by 117 publications

(32 citation statements)

References 61 publications

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“…Recently, Li and co‐workers developed an interesting copper‐catalyzed intramolecular C–H oxidation/acylation of formyl‐ N ‐arylformamides to afford the corresponding indoline‐2,3‐diones 8. Subsequently, a series of methods for transition‐metal‐catalyzed C–H oxidation were documented,9 including the copper‐catalyzed intramolecular oxidative C(sp 3 )–H amidation of 2‐aminoacetophenones,9a the copper‐mediated C–H oxidation and C–N cross‐coupling of 2′‐aminoacetophenones,9b as well as oxidative palladium‐catalyzed CH/NH double carbonylation 9c. Furthermore, several other protocols have been established, including ylide‐mediated carbonyl homologations,10 selenium‐mediated oxidations,11 modified Sandmeyer reactions,12 I 2 ‐catalyzed synthesis of isatins from 2′‐aminoacetophenones,13a and I 2 ‐mediated oxidative amidation of sp, sp 2 , and sp 3 C–H bonds 13b…”

Section: Introductionmentioning

confidence: 99%

Titania‐Supported Gold Nanoparticles as Efficient Catalysts for the Oxidation of Cellobiose to Organic Acids in Aqueous Medium

Amaniampong

Jia

et al. 2014

ChemCatChem

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Titania‐supported gold nanoparticles were prepared by using the deposition–precipitation method, followed by reduction under a hydrogen flow. The catalytic activity of these as‐prepared catalysts was explored in the oxidation of cellobiose to gluconic acid with molecular oxygen, and the properties of these catalysts were examined by using XRD, TEM, temperature‐programmed desorption of NH3, energy‐dispersive X‐ray spectroscopy, UV/Vis, and X‐ray photoemission spectroscopy (XPS). The catalyst sample reduced at high temperature demonstrated an excellent catalytic activity in the oxidation of cellobiose. The characterization results revealed the strong metal–support interaction between the gold nanoparticles and titania support. Hydrogen reduction at higher temperatures (usually >600 °C) plays a vital role in affording a unique interface between gold nanoparticles and titania support surfaces, which thus improves the catalytic activity of gold/titania by fine‐tuning both the electronic and structural properties of the gold nanoparticles and titania support.

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Section: Introductionmentioning

confidence: 99%

Titania‐Supported Gold Nanoparticles as Efficient Catalysts for the Oxidation of Cellobiose to Organic Acids in Aqueous Medium

Amaniampong

Jia

et al. 2014

ChemCatChem

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“…63 The reaction proceeds under atmospheric pressure of CO and has been proposed to involve an N-H activation by the palladium complex, followed by coordination and insertion of CO. The resulting carbamoyl intermediate undergoes another CO insertion which is followed by a C-H activation to give a palladacycle intermediate.…”

Section: (3+1+1) Annulationsmentioning

confidence: 99%

“…In 2015 the Lei research group reported ap alladiumcatalyzed double carbonylation of anilides to form isatins (Scheme 38). [63] Thereaction proceeds under an atmospheric Scheme 37. Pd-catalyzeda nnulation between ap henylindole and an alkyne.…”

Section: (3+ +1+ +1) Annulationsmentioning

confidence: 99%

Metal‐Catalyzed Annulations through Activation and Cleavage of C−H Bonds

2016

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Abstract:The exponential increase in the number of catalytic transformations that involve a metal-promoted activation of hitherto considered inert C-H bonds is promoting a paradigmatic change in the field of synthetic chemistry. While most reactions involving C-H activations consist of simple functionalizations or additions, recent years have witnessed a boost on related transformations that can be formally considered as cycloaddition processes. These transformations are particularly appealing from a synthetic perspective because they allow the conversion of readily available substrates into highly valuable cyclic products in a rapid and sustainable manner. In many cases, these annulations involve the formation of metallacyclic intermediates that resemble those proposed for standard metalcatalyzed cycloadditions of unsaturated precursors.

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“…Lei et al. beschrieben 2015 eine palladiumkatalysierte doppelte Carbonylierung von Aniliden zur Synthese von Isatinen (Schema ) . Die Reaktion wird unter Atmosphärendruck von CO durchgeführt und verläuft vermutlich über eine N‐H‐Aktivierung durch den Palladiumkomplex und anschließende Koordination und Insertion von CO. Das entstehende Carbamoylintermediat geht eine weitere CO‐Insertion ein, der eine C‐H‐Aktivierung zum palladacyclischen Intermediat folgt.…”

Section: Anellierungen Mit Migratorischer Insertion Vor Der C‐h‐aktiunclassified

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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From Anilines to Isatins: Oxidative Palladium‐Catalyzed Double Carbonylation of CH Bonds

Cited by 117 publications

References 61 publications

Titania‐Supported Gold Nanoparticles as Efficient Catalysts for the Oxidation of Cellobiose to Organic Acids in Aqueous Medium

Titania‐Supported Gold Nanoparticles as Efficient Catalysts for the Oxidation of Cellobiose to Organic Acids in Aqueous Medium

Metal‐Catalyzed Annulations through Activation and Cleavage of C−H Bonds

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

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