Effective hydrogenation of carbon-carbon triple bonds by NaBH4/PdCl2 in polyethylene glycol/CH2Cl2: Usefulness of peg in synthetic reactions

Suzuki, Nobutaka; Kaneko, Y.; Tsukanaka, T.; Nomoto, Tateo; Ayaguchi, Y.; Izawa, Yasuji

doi:10.1016/s0040-4020(01)96634-7

Cited by 15 publications

(3 citation statements)

References 25 publications

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“…Finally, it was found that the transformation could be achieved by using NaBH 4 in PEG 200 and CH 2 Cl 2 in the presence of 10 mol-% PdI 2 (or PdCl 2 ). [20] Using this method, the alcohol obtained from 10a by reduction with NaBH 4 in MeOH cleanly afforded the pure semi-hydrogenation product (Z-alkene). After re-oxidation of the pseudo-benzylic alcohol function with MnO 2 , the aldehyde 11 was obtained in 45 % overall yield from 10a.…”

Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis and Biological Evaluation of Ferrocene‐Containing 5‐Hydroxyeicosatetraenoic Acid Analogues

et al. 2011

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The stereoselective synthesis of a set of four stable 5-hydroxyeicosatetraenoic acid (HETE) analogues with a ferrocene backbone is described. The common substructure of all HETEs, the (2E,4Z)-1-hydroxyhexadiene moiety, was formally replaced by a ferrocenylmethanol fragment. Whereas the hydrophilic side chain remained the same as that of 5-HETE (butyrate), the lipophilic side chain was simplified by replacing the "natural" (Z,Z)-1,4-decadiene side chain with (Z)-1-heptene, 1-heptyne, 1-octyne, or phenylacetylene. As a key building block, Kagan's chiral acetal (derived from ferrocenecarbaldehyde) was used for the stereoselective generation of the planar-chiral substructure through diastereoselective ortho-lithiation and subsequent formylation, methoxycarbonylation or iodination, respectively. The lipophilic side chain was installed either by a "salt-free" Wittig reaction or (better) by Pd-catalyzed Sonogashira coupling. The

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Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis and Biological Evaluation of Ferrocene‐Containing 5‐Hydroxyeicosatetraenoic Acid Analogues

et al. 2011

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“…Polyethylene glycol (PEG-400) is an excellent substitute for crown ethers and it has been used as a co-solvent in the reduction of carbon-carbon triple or double bonds by NaBH 4 /PdCl 2 in PEG-400/CH 2 Cl 2 , where PdCl 2 is used in catalytic quantities. 8 Using the system of NaBH 4 /1,4-dioxane/CoCl 2 /PEG-400 we anticipated a simple and selective reduction of the 6-imino group of 2c.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 6-imino-5-tetrahydro-1H-2-pyrrolylidenhexahydro-2,4-pyrimidinediones as intermediates for the synthesis of C-azanucleosides

Martirosyan

Tamazyan

Gasparyan

et al. 2010

Tetrahedron Letters

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“…Lithium aluminum hydride (LiAlH4) is a powerful reducing agent, thus its high reactivity has a disadvantage in most of the organic synthesis that cannot be used for selective reduction. By contrast, NaBH4 is a less powerful reducing agent that is comparatively safe for the hydrogenation [28][29][30][31][32], even though it can be used in its solid form. Sodium borohydride is a commonly used reagent primarily for the selective reduction of carbonyl compounds [33,34], p-nitrophenol to p-aminophenol [35], while being combined with metal salts and various solvents which provide an excellent variety of reducing systems.…”

Section: 4'-bipyridinementioning

confidence: 99%

Mixed-Ligand Ni(II), Co(II) and Fe(II) Complexes as Catalysts for Esterification of Biomass-Derived Levulinic Acid with Polyol and in Situ Reduction via Hydrogenation with NaBH4

Lee

Hossain

2019

Journal of Renewable Materials

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Synthesizing polyol-based ester from biomass feedstocks for the preparation of biolubricant overcomes the dependence on petroleum oil usage. Albeit biomass-derived bio-oil is an alternative for the production of polyol ester, upgrading is essential prior to use as biolubricant. Levulinic acid (LA), obtained from bio-oil was applied for the catalytic esterification with two polyols, e.g., trimethylolpropane (TMP) and pentaerythritol (PE), in the presence of mixedligand Ni(II), Co(II), and Fe (II) complexes as catalyst. New mixed-ligand coordination complexes with empirical formula; [Ni(Phe)(Bpy)Cl].H2O, [Co(Phe)(Bpy)Cl].H2O, and [Fe(Phe)(Tyr)Cl].H2O were synthesized by the reaction of ligands [L-phenylalanine (Phe), 4,4'-bipyridine (Bpy), and L-tyrosine (Tyr)] with metal chloride salts and characterized by elemental analysis, magnetic susceptibility, FTIR, TGA/DTA, powder-XRD, and SEM techniques.This study aims to investigate the catalytic activities of the complexes via esterification reaction of levulinic acid with trimethylolpropane and pentaerythritol. In addition, these catalysts were further employed for the in situ hydrogenation of levulinate esters via NaBH4 at room temperature upon refluxing. Indeed, the iron(II) complex was more potential, exhibiting its efficiency as a homogeneous catalyst for esterification-hydrogenation reaction for synthesizing ester-based oils.

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Effective hydrogenation of carbon-carbon triple bonds by NaBH4/PdCl2 in polyethylene glycol/CH2Cl2: Usefulness of peg in synthetic reactions

Cited by 15 publications

References 25 publications

Stereoselective Synthesis and Biological Evaluation of Ferrocene‐Containing 5‐Hydroxyeicosatetraenoic Acid Analogues

Stereoselective Synthesis and Biological Evaluation of Ferrocene‐Containing 5‐Hydroxyeicosatetraenoic Acid Analogues

Synthesis of 6-imino-5-tetrahydro-1H-2-pyrrolylidenhexahydro-2,4-pyrimidinediones as intermediates for the synthesis of C-azanucleosides

Mixed-Ligand Ni(II), Co(II) and Fe(II) Complexes as Catalysts for Esterification of Biomass-Derived Levulinic Acid with Polyol and in Situ Reduction via Hydrogenation with NaBH4

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