Chiral Dinuclear Vanadium Complex-Mediated Oxidative Coupling of Resorcinols

Sako, M.; Aoki, T.; Zumbrägel, Nadine; Schober, Lukas; Gröger, Harald; Takizawa, Shinobu; Sasai, Hiroaki

doi:10.1021/acs.joc.8b02494

Cited by 33 publications

(14 citation statements)

References 55 publications

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“…[98] Very recently,T akizawa, Sasai, and co-workers developed ad inuclear vanadium complex that mediated the oxidative homocoupling of various 5-arylresorcinols to furnish the corresponding biaryls with up to 98 % ee. [99]…”

Section: Angewandte Chemiementioning

confidence: 99%

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

et al. 2019

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Oxidative aromatic coupling occupies a fundamental place in the modern chemistry of aromatic compounds. It is a method of choice for the assembly of large and bewildering architectures. Considerable effort was also devoted to applications of the Scholl reaction for the synthesis of chiral biphenols and natural products. The ability to form biaryl linkages without any prefunctionalization provides an efficient pathway to many complex structures. Although the chemistry of this process is only now becoming fully understood, this reaction continues to both fascinate and challenge researchers. This is especially true for heterocoupling, that is, oxidative aromatic coupling with the chemoselective formation of a C−C bond between two different arenes. Analysis of the progress achieved in this field since 2013 reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface‐assisted (cyclo)dehydrogenation, and developing new reagents.

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Section: Angewandte Chemiementioning

confidence: 99%

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

et al. 2019

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“…More recently, Sasai and Takizawa developed a more general asymmetric oxidative coupling of resorcinols 7g,o-aa catalyzed by novel designed dibrominated dinuclear vanadium(V) complex 12 in toluene [18]. The process was performed under air in the presence of 5 mol% of this catalyst at 70°C, leading to the corresponding chiral biresorcinols 8g,o-aa in low to excellent yields (29-93%) and moderate to very high enantioselectivities (36-97% ee), as illustrated in Scheme 9.…”

Section: Enantioselective Vanadium-catalyzed Oxidative Couplingsmentioning

confidence: 99%

“…Oxidative coupling of resorcinols catalyzed by dibrominated dinuclear vanadium(V) complex 12 in toluene [18]. of a 3-hydroxycarbazole such as sorazolon E [19].…”

Section: (10 Mol%)mentioning

confidence: 99%

Enantioselective vanadium-catalyzed transformations. An update

Pellissier

2020

Coordination Chemistry Reviews

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“…Jüngst entwickelten Takizawa, Sasai et al. einen zweikernigen Vanadiumkomplex, der die oxidative Homokupplung verschiedener 5‐Arylresorcine vermittelt und die entsprechenden Biaryle mit bis zu 98 % ee liefert …”

Section: Intermolekulare Oxidative Aromatische Kupplungunclassified

Syntheseanwendungen der oxidativen aromatischen Kupplung – von Biphenolen zu Nanographenen

et al. 2019

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Die oxidative aromatische Kupplung nimmt einen grundlegenden Platz in der modernen Arenchemie ein. Sie ist das Mittel der Wahl für den Aufbau großer, komplizierter Molekülarchitekturen. Auch die Scholl‐Reaktion und ihre Anwendungen in der Synthese chiraler Biphenole und Naturstoffe sind stark beforscht. Die Möglichkeit, Biarylverknüpfungen ohne Vorfunktionalisierung herzustellen, bietet einen effizienten Weg zu vielen komplexen Strukturen. Obwohl die Chemie hinter diesem Prozess erst jetzt nach und nach voll verstanden wird, ist er weiterhin eine Quelle der Inspiration. Dies trifft besonders auf Heterokupplungen zu, d. h. oxidative, aromatische Kupplungen unter chemoselektiver C‐C‐Bindungsbildung zwischen zwei verschiedenen Arenen. Eine Analyse der Fortschritte in diesem Feld seit 2013 zeigt, dass zahlreiche Gruppen hierzu beigetragen haben – durch die Entdeckung neuer struktureller Möglichkeiten, die Erweiterung zu oberflächengestützten (Cyclo)dehydrierungen und die Entwicklung neuer Reagenzien.

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Chiral Dinuclear Vanadium Complex-Mediated Oxidative Coupling of Resorcinols

Cited by 33 publications

References 55 publications

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Enantioselective vanadium-catalyzed transformations. An update

Syntheseanwendungen der oxidativen aromatischen Kupplung – von Biphenolen zu Nanographenen

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