Regiodiverse Three‐Component Synthesis of Arenes

Danz, Michael; Hilt, Gerhard

doi:10.1002/adsc.201000832

Cited by 31 publications

(15 citation statements)

References 33 publications

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“…The research groups of Müllen148 and Hilt149 reported that tribenzo[ fg , ij , rst ]pentaphene derivatives such as 161 are formed exclusively rather than tetrabenzoanthracene 162 (CH 2 Cl 2 /MeNO 2 solution, Scheme ) in the oxidation of triphenylene precursors 160 14b. In one of these cases, the authors noted that neither AlCl 3 nor MeSO 3 H are effective under these conditions.…”

Section: Oxidative Aromatic Couplingmentioning

confidence: 99%

Comparison of Oxidative Aromatic Coupling and the Scholl Reaction

et al. 2013

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Does the dehydrogenative coupling of aromatic compounds mediated by AlCl3 at high temperatures and also by FeCl3, MoCl5, PIFA, or K3[Fe(CN)6] at room temperature proceed by the same mechanism in all cases? With the growing importance of the synthesis of aromatic compounds by double C-H activation to give various biaryl structures, this question becomes pressing. Since some of these reactions proceed only in the presence of non-oxidizing Lewis acids and some only in the presence of certain oxidants, the authors venture the hypothesis that, depending on the electronic structure of the substrates and the nature of the "catalyst", two different mechanisms can operate. One involves the intermediacy of a radical cation and the other the formation of a sigma complex between the acid and the substrate. The goal of this Review is to encourage further mechanistic studies hopefully leading to an in-depth understanding of this phenomenon.

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Section: Oxidative Aromatic Couplingmentioning

confidence: 99%

Comparison of Oxidative Aromatic Coupling and the Scholl Reaction

et al. 2013

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“…The synthesis was initiated by a regioselective ruthenium‐catalysed enyne metathesis for the generation of the 1,3‐diene 17 , which was not isolated. In the next step of the one‐pot procedure, the regiodiverse cobalt‐catalysed Diels–Alder reaction was applied utilising a py‐imine ligand and the second alkyne, in this case trimethylsilylacetylene, so that the 1,3,5‐trisubstituted 1,4‐cyclohexadiene intermediate 18 was generated, before the synthesis of arene 19 was accomplished upon DDQ oxidation . Fortunately, both regioisomers can be generated in the cobalt‐catalysed Diels–Alder reactions by applying two different ligand designs (compare Scheme ).…”

Section: Methodsmentioning

confidence: 99%

1,4‐Cyclohexadienes—Easy Access to a Versatile Building Block via Transition‐Metal‐Catalysed Diels–Alder Reactions

Hilt

2014

The Chemical Record

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1,4-Cyclohexadiene derivatives are easily accessed via transition-metal cycloadditions of 1,3-dienes with alkynes. The mild reaction conditions of several transition-metal-catalysed reactions allows the incorporation of various functional groups to access functionalised 1,4-cyclohexadienes. The control of the regiochemistry in the intermolecular cobalt-catalysed Diels-Alder reaction is realised utilising different ligand designs. The functionalised 1,4-cyclohexadiene derivatives are valuable building blocks in follow-up transformations. Finally, the oxidation of the 1,4-cyclohexadienes can be accomplished under mild conditions to generate the corresponding arene derivatives.

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“…Die Gruppen von Müllen148 und Hilt149 berichteten, dass bei der Oxidation einer Oligophenylen‐Vorstufe wie 160 ausschließlich Tribenzo[ fg , ij , rst ]pentaphen‐Derivate des Typs 161 und nicht Tetrabenzoanthracen 162 (CH 2 Cl 2 /MeNO 2 ‐Lösung) gebildet werden (Schema ) 14b. In einem dieser Fälle bemerkten die Autoren, dass weder AlCl 3 noch MeSO 3 H unter diesen Bedingungen wirksam sind.…”

Section: Oxidative Aromatische Kupplungunclassified

Oxidative aromatische Kupplung und Scholl‐Reaktion im Vergleich

et al. 2013

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Läuft die durch AlCl3 bei hoher Temperatur und auch durch FeCl3, MoCl5, PIFA oder K3[Fe(CN)6] bei Raumtemperatur vermittelte, dehydrierende Kupplung aromatischer Verbindungen in allen Fällen nach dem gleichen Mechanismus ab? Durch die wachsende Bedeutung der Synthese aromatischer Verbindungen durch doppelte C‐H‐Aktivierung, die zu unterschiedlichen Biarylen führt, wird diese Frage dringlicher. Da einige dieser Reaktionen nur in Gegenwart nichtoxidierender Lewis‐Säuren ablaufen und andere nur in Gegenwart bestimmter Oxidationsmittel, wagen die Autoren die Hypothese, dass abhängig von der elektronischen Struktur der Substrate und der Natur des “Katalysators” zwei unterschiedliche Mechanismen ablaufen können. Der eine verläuft über ein Radikalkation als Intermediat, der andere über die Bildung eines Sigma‐Komplexes zwischen Säure und Substrat. Das Ziel dieses Aufsatzes ist es, weitere mechanistische Studien anzuregen, die zu einem eingehenden Verständnis dieses Phänomens führen sollen.

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Regiodiverse Three‐Component Synthesis of Arenes

Cited by 31 publications

References 33 publications

Comparison of Oxidative Aromatic Coupling and the Scholl Reaction

Comparison of Oxidative Aromatic Coupling and the Scholl Reaction

1,4‐Cyclohexadienes—Easy Access to a Versatile Building Block via Transition‐Metal‐Catalysed Diels–Alder Reactions

Oxidative aromatische Kupplung und Scholl‐Reaktion im Vergleich

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