Reduction of carbonyl compounds by using polymethylhydro-siloxane: reactivity and selectivity

Kobayashi, Yuichi; Takahisa, Eisuke; Nakano, Miwa; Watatani, Kengo

doi:10.1016/s0040-4020(96)01092-7

Cited by 73 publications

(29 citation statements)

References 42 publications

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“…4-Isopropylcyclohexanecarboxylic acid (cis and trans mixture; Table 7, entry 4): Cyclohexane-1,4-dicarboxylic acid (cis and trans mixture; Table 7 (23). The 1 H NMR spectrum of the product was identical with that of an authentic sample from Tokyo Chemical Industry Co., Ltd.…”

Section: Arene Hydrogenation In Iproh (Tables 6-16)mentioning

confidence: 79%

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Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions

Maegawa

Akashi

Yaguchi

et al. 2009

Chemistry A European J

134

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An efficient and practical arene hydrogenation procedure based on the use of heterogeneous platinum group catalysts has been developed. Rh/C is the most effective catalyst for the hydrogenation of the aromatic ring, which can be conducted in iPrOH under neutral conditions and at ordinary to medium H(2) pressures (<10 atm). A variety of arenes such as alkylbenzenes, benzoic acids, pyridines, furans, are hydrogenated to the corresponding cyclohexyl and heterocyclic compounds in good to excellent yields. The use of Ru/C, less expensive than Rh/C, affords an effective and practical method for the hydrogenation of arenes including phenols. Both catalysts can be reused several times after simple filtration without any significant loss of catalytic activity.

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Section: Arene Hydrogenation In Iproh (Tables 6-16)mentioning

confidence: 79%

“…The 1 H NMR spectrum of the product was identical with that in the literature. [23] 4-tert-Butylcyclohexanol (cis and trans mixture; (79), 57 (100). The 1 H NMR spectrum of the product was identical with that in the literature.…”

Section: Arene Hydrogenation In Iproh (Tables 6-16)mentioning

confidence: 99%

Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions

Maegawa

Akashi

Yaguchi

et al. 2009

Chemistry A European J

134

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“…[309] Bei der [310] können auch Reduktionen durch Hydrosilane katalysiert werden, speziell durch Fluoridionen. Später wurden Trialkoxy-und Trichlorsilane zusammen mit Polymethylhydrosilan (PMHS) verwendet, [311] weil sie zur Bildung hyperkoordinierter Siliciumkomplexe mit höherem Reduktionsvermögen neigen. Beispielsweise lässt sich Trimethoxysilan mit einer Reihe chiraler anionischer Katalysatoren so aktivieren, [312] dass Acetophenone enantioselektiv reduziert werden (Schema 88).…”

Section: Lewis-base-katalysierte Propargylierung Und Allenylierung Vounclassified

Lewis‐Base‐Katalyse in der organischen Synthese

2008

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Das Erbe von Gilbert Newton Lewis (1875–1946) ist im Wörterbuch der chemischen Bindung und Reaktivität allgegenwärtig. Die Bedeutung seines Konzepts der Donor‐Akzeptor‐Bindung kommt in den eponymen Grundbegriffen für Elektronenpaarakzeptoren (Lewis‐Säuren) und ‐donoren (Lewis‐Basen) zum Ausdruck. Lewis erkannte, dass Säuren nicht automatisch Wasserstoff enthalten müssen (Brønsted‐Säuren) und trug so zum Sturz des “modernen Protonenkults” bei. Seine Entdeckung läutete zunächst die Entwicklung von Lewis‐Säuren als Reagentien und Katalysatoren für organische Reaktionen ein, in den letzten Jahren wurde aber offensichtlich, dass für diese Zwecke auch Lewis‐Basen eingesetzt werden können. Bezüglich der Beschleunigung chemischer Reaktionen ergänzen Lewis‐Basen die entsprechenden Lewis‐Säuren nicht nur elektronisch: Tatsächlich können Lewis‐Basen die Elektrophilie wie auch die Nucleophilie der Verbindungen verstärken, an die sie gebunden werden. Diese unterschiedliche Reaktivität resultiert in einer bemerkenswerten Vielfalt Lewis‐Base‐katalysierter Reaktionen.

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“…Although polysiloxanes bearing a substituted aryl group are not available commercially, such compounds can be synthesized using a commercially available polysiloxane bearing a silicon-hydrogen bond, PMHS [30][31][32][33] by employing the palladium-catalyzed arylation of triethoxysilane with aryl iodides developed by Masuda [34,35]. The method was applied for the arylation of PMHS as a silane species.…”

Section: Resultsmentioning

confidence: 99%

Silicone as an organosilicon reagent for the palladium-catalyzed cross-coupling reaction

Suguro

Yamamura

Koike

et al. 2007

Reactive and Functional Polymers

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Silicone, poly(diorganosiloxane), serves as an organosilicon reagent for palladium-catalyzed cross-coupling reactions. Treatment of poly[(aryl)methylsiloxane], poly[(alkenyl)methylsiloxane], or cyclic oligosiloxanes with various aryl iodides in the presence of silver(I) oxide (Ag 2 O) or tetrabutylammonium fluoride (TBAF) and a catalytic amount of palladium affords the corresponding cross-coupling product in a good to excellent yield. The reaction of silicone with aryl chlorides in the presence of K 2 CO 3 /H 2 O as an activator proceeded to afford biaryl derivatives in moderate to excellent yields. A wide range of aryl chlorides bearing an electron-donating or electron-withdrawing substituent on the aromatic ring are tolerated.

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Reduction of carbonyl compounds by using polymethylhydro-siloxane: reactivity and selectivity

Cited by 73 publications

References 42 publications

Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions

Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions

Lewis‐Base‐Katalyse in der organischen Synthese

Silicone as an organosilicon reagent for the palladium-catalyzed cross-coupling reaction

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