A one-pot oxidation–imine formation–reduction route from alcohols to amines using manganese dioxide–sodium borohydride: the synthesis of naftifine

Kanno, Hisashi; Taylor, Richard J.K.

doi:10.1016/s0040-4039(02)01722-7

Cited by 39 publications

(18 citation statements)

References 11 publications

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“…Sithambaram reported direct catalytic synthesis of imines from alcohols using manganese octahedral molecular sieves [35], Taylor described a tandem oxidation-imine formation process from alcohols with active manganese oxide [36,37], Korich developed a facile, one pot procedure to afford diarylimines [38], Macho reported one stage preparation of Schiff's bases from nitroarenes, aldehydes and carbon monoxide in the presence of water [39], tandem nitroarene reduction and intramolecular Schiff base condensation to provide heteroarenes has also been reported [40,41].…”

Section: Introductionmentioning

confidence: 99%

One Pot Synthesis of Imines from Aromatic Nitro Compounds with a Novel Ni/SiO2 Magnetic Catalyst

Zheng

et al. 2008

Catal Lett

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We have successfully prepared a novel Ni/SiO 2 magnetic catalyst, and put it into the process of one pot synthesis of imines directly from aromatic nitro compounds and aldehydes for the first time. The catalyst has been characterized by XRD, IR, TEM, SEM, TPR, H 2 -TPD and XPS. The prominent merits of the Ni/SiO 2 magnetic catalyst passivated with a gas mixture are that it can be stored safely in air below 423 K and needs no activation before use. In the catalytic test, most conversion and selectivity is almost up to 100%, and it is found that the catalyst is highly efficient, stable, and reusable for the synthesis of imines.

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Section: Introductionmentioning

confidence: 99%

One Pot Synthesis of Imines from Aromatic Nitro Compounds with a Novel Ni/SiO2 Magnetic Catalyst

Zheng

et al. 2008

Catal Lett

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“…Facile synthesis of allylic amines and thioethers are very important in both organic and bioorganic chemistry . Selected examples include the calcium channel blocker, flunarizine; the antifungal drug, naftifine; and s ‐allyl cysteine . A transition‐metal‐catalyzed reaction of activated allylic alcohol derivatives, such as allylic halides, acetate, carboxylates, and carbonates, has proven to be one of the most powerful methods .…”

Section: Figurementioning

confidence: 99%

Iron‐Catalyzed Synthesis of Amines and Thioethers Directly from Allylic Alcohols

et al. 2018

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As traightforward and efficient approach for the synthesis of allylic amines and thioethers has been developed by an iron-catalyzed cross-coupling reaction using diphosphitel igand.T he reaction between allylic alcohols and amines/thiolsg ave allylic amine and thioester.T he method is compatible with variousf unctional groups,a ffording products with high yield and monoallylation selectivity.Facile synthesis of allylic amines and thioethers are very important in both organic and bioorganic chemistry. [1] Selected examplesi nclude the calcium channel blocker,f lunarizine; [1e] the antifungal drug, naftifine; [1f] and s-allyl cysteine. [1j] At ransitionmetal-catalyzed reaction of activated allylic alcohol derivatives, such as allylic halides, acetate, carboxylates, and carbonates, has provent ob eo ne of the most powerful methods. [2] Althought he direct catalytic substitutiono fa llylic alcohols is economical and attractive method, forming water as the only by-product;h owever, such alcohols are difficult to activate because of ap oor leavinga bility of the hydroxyl group.In the last decades, few groups have successfully developed palladium-and platinum-catalyzed reactions of allylic alcohols via metal-p-allyl species to form CÀCa nd CÀXb onds. Ozawa and co-workersr eported ad irect amination of allylic alcohols catalyzed by p-allyl-palladium complexesc ontaining diphosphinidenecyclobutenel igand. [3] Mashima and co-workers synthesized allylic amines using Pt-DPEphos complexes, which acted as an excellent catalyst for the high catalyst activity and high monoallylation selectivity. [4] The recent work of Sarkar [5] and Beller [6] is also interesting. Particularly,O shima,I kariya, Breit, and other groups have also made their contributionst o the developmentoft his methodology. [7] Nevertheless,o nly av ery few earth-abundant and cheap first-row transition-metal catalysts for the conversion of allylic alcohols to allylic amines and thioethers have been reported. [8] In 2008, Jana reportedt he FeCl 3 -catalyzed direct substitution of benzylic and allylic alcohols with carboxamides. [8a] Cossy developeda ni ntramolecular allyl substituent reaction catalyzed by FeCl 3 . [8b] Nickel-diphosphine catalytic system was reported by Mashima. [8c] Recently,S undararaju reported ad irect allylic amination catalyzed by an iron catalystt hrough an oxidation/ reduction pathway,a nd also realizedt he synthesis of pyrrole. [8d, e] Herein, we report an ew approachf or the synthesis of allylic amines and thioethersb ya ni ron-catalyzed cross-coupling reaction directly from allylic alcohols (Figure 1) using diphosphite ligand with distinctive electronic and steric effect.Optimization of the reaction conditions was carriedo ut with cinnamyl alcohol (1a)a nd aniline (2a)a ss tandard substrates. As shown in Table 1, al arge variation in reactivity was observed, depending on the ligand, catalyst, solvent, and temperature used in the reactions. In the presence of Fe(OTf) 2 as catalyst, variousl igands were examined. Yield was ...

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“…MnO 2 is a typical multiple-phase oxide [6][7][8] that has attracted considerable attention in the field of catalysis owing to its low cost and high stability [9][10][11][12][13]. Specifically, it has been widely employed as a heterogeneous catalyst in organic synthesis [10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

“…Specifically, it has been widely employed as a heterogeneous catalyst in organic synthesis [10][11][12][13]. However, most of the studies on MnO 2 catalysis have not investigated the influence of its crystalline phase on its catalytic performance.…”

Section: Introductionmentioning

confidence: 99%

Crystalline-phase-dependent catalytic performance of MnO2 for aerobic oxidation reactions

Huang

Yang

et al. 2017

Sci. China Mater.

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Knowledge of the catalytic performances of different crystalline phases of a material is vital for the development of superior catalysts. In this study, different phases of MnO 2 (α, β, γ, and δ) have been prepared by the oxidation of Mn 2+, and their catalytic performances were evaluated using the aerobic oxidation of benzyl alcohol to benzaldehyde as a model reaction. α-MnO 2 promoted the reaction to the highest yield. However, when the yields were normalized by the corresponding surface areas, δ-MnO 2 exhibited the highest specific activity and α-MnO 2 the lowest, indicating that the diverse microstructures resulting from the crystalline phase have a profound effect on catalytic performance. α-MnO 2 showed the highest catalytic stability, resulting from its unchanged composition and morphology after use. Informed by the experimental results, a possible reaction mechanism involving the Mars-van Krevelen process was proposed. This work provides useful information for the development of effective catalysts for aerobic oxidation.

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A one-pot oxidation–imine formation–reduction route from alcohols to amines using manganese dioxide–sodium borohydride: the synthesis of naftifine

Cited by 39 publications

References 11 publications

One Pot Synthesis of Imines from Aromatic Nitro Compounds with a Novel Ni/SiO2 Magnetic Catalyst

One Pot Synthesis of Imines from Aromatic Nitro Compounds with a Novel Ni/SiO2 Magnetic Catalyst

Iron‐Catalyzed Synthesis of Amines and Thioethers Directly from Allylic Alcohols

Crystalline-phase-dependent catalytic performance of MnO2 for aerobic oxidation reactions

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