<b>Catalytic Hydrogenation of Organic Compounds by Pentacyanocobaltate(II)</b>

Kwiatek, Jack; Mador, Irving L.; Seyler, Jay K.

doi:10.1021/ja00861a034

Cited by 77 publications

(28 citation statements)

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“…In the early 1960s, Kwiatek and Seyler first reported the use of metal hydrides as catalysts in the hydrogenation of α,β‐unsaturated compounds . The discovery by Halpern, later elegantly developed by Norton, that metal‐hydride hydrogen atom transfer (HAT) proceeded by a free‐radical mechanism opened the door to a wide range of alkene hydrofunctionalisation reactions.…”

Section: Methodsmentioning

confidence: 99%

Hydrogen Atom Transfer‐Mediated Cyclisations of Nitriles

Turner

Murphy

Hirst

et al. 2018

Chemistry A European J

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Hydrogen atom transfer‐mediated intramolecular C−C coupling reactions between alkenes and nitriles, using PhSiH3 and catalytic Fe(acac)3, are described. This introduces a new strategic bond disconnection for ring‐closing reactions, forming ketones via imine intermediates. Of note is the scope of the reaction, including formation of sterically hindered ketones, spirocycles and fused cyclic systems.

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Section: Methodsmentioning

confidence: 99%

Hydrogen Atom Transfer‐Mediated Cyclisations of Nitriles

Turner

Murphy

Hirst

et al. 2018

Chemistry A European J

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“…It has long been known that [CoH(CN) 5 ] 3is capable of hydrogenating nitro-, azoxy-and azo-compounds under mild conditions [49]. It has long been known that [CoH(CN) 5 ] 3is capable of hydrogenating nitro-, azoxy-and azo-compounds under mild conditions [49].…”

Section: Aqueous Two-phase Hydrogenations Of Nitro-compounds Iminesmentioning

confidence: 99%

Two‐Phase Aqueous Hydrogenations

Joó¹,

Kathó²

2006

The Handbook of Homogeneous Hydrogenation

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“…This complex can reduce water to hydrogen (22) and can react reversibly with molecular hydrogen to give a hydride ion [CoIII(CN)~H] 3- (22). Sorbic acid was hydrogenated quantitatively and selectively to 2-hexenoic acid (7,23). Sorbic acid was hydrogenated quantitatively and selectively to 2-hexenoic acid (7,23).…”

Section: Introduction Cmentioning

confidence: 99%

“…During the past 2 years this complex was used for the homogeneous catalytic hydrogenation of conjugated systems. In addition to conjugated systems, epoxides, allylic compounds, various nitrogen-containing compounds, and certain inorganic substrates such as hydrogen peroxide and metal salts were reduced (23,24). In addition to conjugated systems, epoxides, allylic compounds, various nitrogen-containing compounds, and certain inorganic substrates such as hydrogen peroxide and metal salts were reduced (23,24).…”

Section: Introduction Cmentioning

confidence: 99%

“…Due to discrepancies regarding the selectivity of pentaeyanoeobaltate II in the literature (7,(23)(24)(25), addi-tionM analyses, sueh as gas chromatography and IR and UV spectrophotometry, were used for studying the products of hydrogenation of sorbic acid. This degree of selectivity has not been reported for heterogeneous catalytic hydrogenation.…”

Section: Introduction Cmentioning

confidence: 99%

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Homogeneous catalytic hydrogenation of sorbic acid with pentacyanocobaltate II

Mabrouk

Dutton

Cowan

1964

J Americ Oil Chem Soc

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The homogeneous hydrogenation of sodium sorbate, with pentaeyanoeobaltate II used as the catalyst, was followed manometrically at room temperature and atmospheric hydrogen pressure. One mole of hydrogen was absorbed by one mole of sorbate. UV and II~ analyses demonstrated the reduction of sorbate to hexenoate. Gas liquid chromatography (GLC) of hexenoate indicated 82, 17, and 1% yields of 2-,3-, and 4-hexenoates, respectively, with traces of sorbate. Increasing either the period of hydrogenation or the ratio of catalyst to sorbate, or both, did not cause the formation of caproate or change the ratio of the three isomers. Homogeneous catalytic hydrogenation in methanolic solutions showed higher selectivity since 2-hexenoate was present in 96% yield.To standardize GLC columns, hexenoic acid isomers were synthesized by the Knoevenagel condensation. Trans-2-hexenoic and t r~r~s-3-hexenoie acids were prepared in 75 and 85% yields by a condensation of n-butanal and malonic acid in the presence of pyridine and triethanolamine, respectively. Trans-4-hexenoic acid was prepared in 70% yield by condensing diethyl malohate with erotyl bromide. Physical properties, including UV and IR spectra, were determined for the purified synthetic adds and methyl esters.Although the absolute specificity of attack at the 4,5-double bond of sorbic acid was not confirmed, the high degree of selectivity obtained does encourage further study of homogeneous catalysis on higher fatty acids.

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Catalytic Hydrogenation of Organic Compounds by Pentacyanocobaltate(II)

Cited by 77 publications

References 0 publications

Hydrogen Atom Transfer‐Mediated Cyclisations of Nitriles

Hydrogen Atom Transfer‐Mediated Cyclisations of Nitriles

Two‐Phase Aqueous Hydrogenations

Homogeneous catalytic hydrogenation of sorbic acid with pentacyanocobaltate II

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