Synthesis of Homoallylamines by the Addition of Allylic Indium Reagents to Azomethines and Nitriles

Jin, Shun-Ji; Araki, Shuki; Butsugan, Yasuo

doi:10.1246/bcsj.66.1528

Cited by 45 publications

(14 citation statements)

References 11 publications

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“…[169] Thus, product formation can be rationalized by assuming that the allylic radical generated in the oxidative IFET as discussed above, undergoes CÀC heterocoupling with the aaminodiphenylmethyl radical produced according to Scheme 19. In no cases could a product arising from CÀ N heterocoupling be observed. Thus, in contrast to potential thermal routes, which usually involve the use of organometallic reagents, [170] the reaction is regioselective and much easier to perform.…”

Section: à C Coupling Through Semiconductor Photocatalysis Type Bmentioning

confidence: 99%

Semiconductor Photocatalysis—Mechanistic and Synthetic Aspects

2012

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Preceding work on photoelectrochemistry at semiconductor single-crystal electrodes has formed the basis for the tremendous growth in the three last decades in the field of photocatalysis at semiconductor powders. The reason for this is the unique ability of inorganic semiconductor surfaces to photocatalyze concerted reduction and oxidation reactions of a large variety of electron-donor and -acceptor substrates. Whereas great attention was paid to water splitting and the exhaustive aerobic degradation of pollutants, only a small amount of research also explored synthetic aspects. After introducing the basic mechanistic principles, standard experiments for the preparation and characterization of visible light active photocatalysts as well as the investigation of reaction mechanisms are discussed. Novel atom-economic C-C and C-N coupling reactions illustrate the relevance of semiconductor photocatalysis for organic synthesis, and demonstrate that the multidisciplinary field combines classical photochemistry with electrochemistry, solid-state chemistry, and heterogeneous catalysis.

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Section: à C Coupling Through Semiconductor Photocatalysis Type Bmentioning

confidence: 99%

Semiconductor Photocatalysis—Mechanistic and Synthetic Aspects

2012

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“…[169] Dementsprechend kann die Bildung der Homoallylamine über eine C-C-Kupplung der intermediären Allylund a-Aminodiphenylmethylradikale formuliert werden (Schema 19). Im Unterschied zu potenziellen thermischen Synthesen mithilfe metallorganischer Reagentien [170] ist die Reaktion regioselektiv und einfacher durchzuführen.…”

Section: C-c-kupplung Durch Halbleiterphotokatalyse Typ Bunclassified

Halbleiterphotokatalyse – mechanistische und präparative Aspekte

Kisch

2012

Angewandte Chemie

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Basierend auf frühen Arbeiten zur Photoelektrochemie an Halbleitereinkristallelektroden hat das Gebiet der Photokatalyse an Halbleiterpulvern in den letzten drei Dekaden ein erstaunliches Wachstum erlebt. Dies ist in der einzigartigen Fähigkeit anorganischer Halbleiteroberflächen begründet, konzertierte Reduktionen und Oxidationen einer großen Vielzahl von Elektronendonor‐ und Elektronenakzeptorsubstraten zu photokatalysieren. Während die Spaltung von Wasser und der erschöpfende aerobe Abbau von Schadstoffen große Beachtung fanden, befasste sich nur ein kleiner Teil der Forschung mit präparativen Aspekten. Nach Einführung der mechanistischen Grundlagen folgen Standardexperimente zur Herstellung und Charakterisierung von Photokatalysatoren, die mit sichtbarem Licht aktiv sind. Anschließend illustrieren neuartige atomökonomische C‐C‐ und C‐N‐Kupplungsreaktionen die Relevanz der Halbleiterphotokatalyse für die organische Synthese. Beispielhaft zeigen sie, dass in diesem multidisziplinären Gebiet klassische Photochemie mit Elektrochemie, Festkörperchemie und heterogener Katalyse vereint sind.

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“…The first successful results of indium-mediated allylation of nitriles have been reported by Yamamoto and Fujiwara a decade ago (Scheme 20), 7b,21 although allylation of nitrile with allylindate instead of allylindium reagents was reported by Butsugan and coworkers in 1993 (vide infra, Scheme 21). 22 The allylation of nitriles with allylindium reagents was, however, limited to substrates having an electron-withdrawing substituent and an a-proton, as shown in Scheme 20. 7b,21…”

Section: Nitrilesmentioning

confidence: 99%