Synthesis of cyclic carbonates from carbon dioxide and epoxides in the presence of organoantimony compounds as novel catalysts

Nomura, Ryoji; Ninagawa, Akira; Matsuda, Haruo

doi:10.1021/jo01307a002

Cited by 125 publications

(55 citation statements)

References 6 publications

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“…However, an intriguing process which is catalytic in both the metal halide and the Lewis base has been developed by the Nomura, Baba, and Shibata research groups. [287] The insertion of carbon dioxide and isocyanides into oxiranes is a very well known process and is susceptible to catalysis by a number of different methods. [288] In an early study, Ratzenhofer and Kisch reported the accelerating effect of Lewis bases (Ph 3 P and Et 3 N) in combination with relatively hard Lewis acids (for example, AlCl 3 , TiCl 4 , and MoCl 5 ) to effect the insertion of carbon dioxide into propylene oxide at room temperature and pressure.…”

Section: Ligand-accelerated Catalysis With Trialkyltin(iv) Halidesmentioning

confidence: 99%

Lewis Base Catalysis in Organic Synthesis

2008

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The legacy of Gilbert Newton Lewis (1875-1946) pervades the lexicon of chemical bonding and reactivity. The power of his concept of donor-acceptor bonding is evident in the eponymous foundations of electron-pair acceptors (Lewis acids) and donors (Lewis bases). Lewis recognized that acids are not restricted to those substances that contain hydrogen (Brønsted acids), and helped overthrow the "modern cult of the proton". His discovery ushered in the use of Lewis acids as reagents and catalysts for organic reactions. However, in recent years, the recognition that Lewis bases can also serve in this capacity has grown enormously. Most importantly, it has become increasingly apparent that the behavior of Lewis bases as agents for promoting chemical reactions is not merely as an electronic complement of the cognate Lewis acids: in fact Lewis bases are capable of enhancing both the electrophilic and nucleophilic character of molecules to which they are bound. This diversity of behavior leads to a remarkable versatility for the catalysis of reactions by Lewis bases.

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Section: Ligand-accelerated Catalysis With Trialkyltin(iv) Halidesmentioning

confidence: 99%

Lewis Base Catalysis in Organic Synthesis

2008

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“…Die Arbeitsgruppen von Nomura, Baba und Shibata entwickelten eine interessante Reaktion, die sowohl bezüglich des Metallhalogenids als auch bezüglich der Lewis-Base katalytisch abläuft. [287] Die Insertion von Kohlendioxid und Isocyaniden in Oxirane ist eine bekannte Reaktion, die auf verschiedene Weise katalysiert werden kann. [288] [292] Bei der doppelten Aktivierung unterscheiden sich nicht nur die Reaktivitäten, sondern auch die stereochemischen Ergebnisse der beiden Reaktionen, die über offene und geschlossene Übergangszustände verlaufen.…”

Section: Ligandenbeschleunigte Katalyse Mit Trialkylzinn(iv)-halogenidenunclassified

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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“…The cyclic carbonates are widely used as organic synthetic intermediates, aprotic polar solvents, precursors for biomedical applications and as raw materials for engineering plastics. [5] Various catalysts have been developed for the synthesis of cyclic organic carbonates from CO 2 and epoxides, among which several homogeneous and heterogeneized salen complexes, [6] alkali metal halides, [7] organic bases, [8] metal oxides, [9] zeolite, [10] ionic liquids [11] and metal complexes [12] can be mentioned. While the advances have been significant, most of these catalysts currently suffer from low catalyst reactivity, the need for co-solvent or the requirement for high pressure and/or high temperature.…”

Section: Introductionmentioning

confidence: 99%

Conversion of carbon dioxide to cyclic carbonates using diimine Ru(II) complexes as catalysts

Ulusoy

Çetinkaya

Çetınkaya

2008

Applied Organom Chemis

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Cationic diimine Ru(II) complexes were synthesized and tested as catalysts for the formation of cyclic organic carbonates from CO 2 and liquid epoxides (propylene oxide, epichlorohydrine, 1,2-epoxybutane and styrene oxide) which served as both reactant and solvent. The reaction rates not only depended on the type of ligand, but also on reaction conditions such as temperature, pressure, base, the epoxide substrates and the use of an additional solvent. Reaction rates in terms of turnover frequencies up to 4050 mol product mol cat.−1 h −1 at 99% selectivity were achieved by optimizing the diimine ligand as well as the reaction temperature and CO 2 pressure. Consistent with CV measurements, the electron donating group on the p-position of the aryl ring accelerated the reaction rate.

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Synthesis of cyclic carbonates from carbon dioxide and epoxides in the presence of organoantimony compounds as novel catalysts

Cited by 125 publications

References 6 publications

Lewis Base Catalysis in Organic Synthesis

Lewis Base Catalysis in Organic Synthesis

Lewis‐Base‐Katalyse in der organischen Synthese

Conversion of carbon dioxide to cyclic carbonates using diimine Ru(II) complexes as catalysts

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