Gold-catalyzed direct oxidative coupling reactions of non-activated arenes

Kar, Anirban; Mangu, Naveenkumar; Kaiser, Hanns Martin; Tse, Man Kin

doi:10.1016/j.jorganchem.2008.11.016

Cited by 103 publications

(45 citation statements)

References 137 publications

(42 reference statements)

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“…As a case in point, conducting the gold-catalyzed oxidative coupling of arenes described above in the presence of benzene and 4-haloanisoles leads to essentially stochastic mixtures of the cross-coupled biaryl product and the homodimers of each arene. [22] A cross-coupling reaction between arylacetylenes and stoiA C H T U N G T R E N N U N G chiometric arylgoldA C H T U N G T R E N N U N G (III) complexes was demonstrated by Fuchita et al [23] A range of various arylgoldA C H T U N G T R E N N U N G (III) complexes 17 stabilized by 2,6-lutidine were prepared from the corresponding arenes and goldA…”

Section: Oxidative Coupling Reactions Involvingmentioning

confidence: 99%

Au^I/Au^III Catalysis: An Alternative Approach for CC Oxidative Coupling

Hopkinson

Gee

Gouverneur

2011

Chemistry A European J

316

119

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When reacted in the presence of external oxidants, gold complexes are capable of catalyzing oxidative homo- and cross-coupling reactions involving the formation of new C-C bonds. Over the last few years, several cascade processes have been reported in which coupling is preceded by a gold-mediated aryl C-H functionalization or nucleophilic addition. These reactions combine the unique reactivity of gold with oxidative coupling, enabling the construction of C-C bonds between coupling partners that are not easily accessed using alternative catalysts. In this Concept paper, the development of gold-catalyzed oxidative coupling reactions is discussed focusing on C-C bond-forming reactions of broad synthetic appeal.

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Section: Oxidative Coupling Reactions Involvingmentioning

confidence: 99%

Au^I/Au^III Catalysis: An Alternative Approach for CC Oxidative Coupling

Hopkinson

Gee

Gouverneur

2011

Chemistry A European J

316

119

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“…[33a, 34] Ihre detaillierte Untersuchung der Reaktionsbedingungen ergab, dass zwei Faktoren die Chemoselektivität entscheidend bestimmen: 1) die Menge an Trifluoressigsäure (TFA) und 2) das Verhältnis der Kupplungspartner. Letzteres erleichterte vermutlich zunächst die Aktivierung der weniger reaktiveren Komponente, da diese im Überschuss eingesetzt wurde.…”

Section: F Glorius Et Alunclassified

“…[111,34] [112] Schema 24. Gold-katalysierte Acetoxylierung von Arenen mit PIDA von Wang et al [104] und Michelet et al [105] Schema 25.…”

Section: C-n-bindungsbildungunclassified

Ohne dirigierende Gruppen: übergangsmetallkatalysierte C‐H‐Aktivierung einfacher Arene

et al. 2012

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Der Einsatz von koordinierenden Gruppen als dirigierende Gruppen ist eine zuverlässige Methode zur Kontrolle von Reaktivität und Selektivität bei der Aktivierung von Aryl‐C‐H‐Bindungen. Im Hinblick auf die Anwendbarkeit von C‐H‐Aktivierungen in der Synthese besteht derzeit ein großes Interesse daran, Reaktionen zu entwickeln, in denen völlig auf dirigierende Gruppen verzichtet werden kann und somit die Funktionalisierung einfacher Benzolderivate möglich wird. Dieser Ansatz erfordert jedoch neue Strategien zur Reaktivitäts‐ und Selektivitätskontrolle. In diesem Kurzaufsatz werden aktuelle Fortschritte in dem noch jungen Gebiet der nicht‐chelatvermittelten C‐H‐Aktivierung diskutiert, wobei einige inspirierende Beispiele zur Reaktivitäts‐ und Selektivitätsinduktion hervorgehoben werden.

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“…In general, the catalytic potential of gold nanoparticles for oxidation reactions was described before [16][17][18][19][20][21][22]. Even Lewis-acid properties for noble metal nanoparticles seem conceivable because of their high electron affinity [23][24]. To clear this point, gold nanoparticles as well as silver and copper nanoparticles were investigated for their catalytic potential in the cyclization/aromatization sequence.…”

Section: Heterogeneous Catalystsmentioning

confidence: 99%

Heterogeneous Catalyzed Pyridine Synthesis using Montmorillionite and Nanoparticle‐Impregnated Alumina in a Continuous Micro Flow System

Abahmane¹,

Knauer²,

Ritter³

et al. 2009

Chem Eng & Technol

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The synthesis of pyridine derivatives was investigated using a combined micro flow-through system. Therefore, two different heterogeneous catalyst assemblies were used subsequently under different temperature conditions. The investigated pyridine synthesis method includes three reaction steps: at first, an enamine has to be formed by a condensation reaction of methyl ketone and propargylamine. Secondly, a pericyclic reaction of the enamine is needed to form dihydropyridine derivatives. Finally, the dihydropyrimidines received have to be oxidized to yield the desired pyridine derivative. The propargylamine used tends towards side reactions even if activating catalysts are present at elevated temperatures. To reach high yields for the overall process, each reaction step demands for a specific catalyst and suited reaction conditions. Hence, the reaction sequence was separated into two consecutive steps. For the initial condensation reaction, montmorillionite was investigated as heterogeneous catalyst. For the subsequent reaction steps, different types of nanoparticles impregnated on alumina were investigated as oxidation catalyst, using air as oxidation agent. Here, the results and optimized process conditions for the conversion of aliphatic and aromatic methyl ketones are presented. As a result, the separation of the reaction steps by application of the two-step microreactor system leads to a significant improvement of the process performance. The reaction time was reduced significantly to about 20 minutes without reduction of the product turnover in several cases.

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Gold-catalyzed direct oxidative coupling reactions of non-activated arenes

Cited by 103 publications

References 137 publications

Au^I/Au^III Catalysis: An Alternative Approach for CC Oxidative Coupling

Au^I/Au^III Catalysis: An Alternative Approach for CC Oxidative Coupling

Ohne dirigierende Gruppen: übergangsmetallkatalysierte C‐H‐Aktivierung einfacher Arene

Heterogeneous Catalyzed Pyridine Synthesis using Montmorillionite and Nanoparticle‐Impregnated Alumina in a Continuous Micro Flow System

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Gold-catalyzed direct oxidative coupling reactions of non-activated arenes

Cited by 103 publications

References 137 publications

AuI/AuIII Catalysis: An Alternative Approach for CC Oxidative Coupling

AuI/AuIII Catalysis: An Alternative Approach for CC Oxidative Coupling

Ohne dirigierende Gruppen: übergangsmetallkatalysierte C‐H‐Aktivierung einfacher Arene

Heterogeneous Catalyzed Pyridine Synthesis using Montmorillionite and Nanoparticle‐Impregnated Alumina in a Continuous Micro Flow System

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Product

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Au^I/Au^III Catalysis: An Alternative Approach for CC Oxidative Coupling

Au^I/Au^III Catalysis: An Alternative Approach for CC Oxidative Coupling