Summary: Addition of hydrogen to a compound, especially to an unsaturated fat or fatty acid. (From Stedman, 26th ed)
- Maenaka Y, Suenobu T, Fukuzumi S. Hydrogen evolution from aliphatic alcohols and 1,4-selective hydrogenation of NAD+ catalyzed by a [C,N] and a [C,C] cyclometalated organoiridium complex at room temperature in water. J Am Chem Soc. 2012;134:9417-27 pubmed publisher..9) under ambient conditions. The 1,4-selective catalytic hydrogenation of ?-nicotinamide adenine dinucleotide (NAD(+)) by ethanol was also made possible by the complex 1 to produce ..
- Bartoszewicz A, Ahlsten N, Martín Matute B. Enantioselective synthesis of alcohols and amines by iridium-catalyzed hydrogenation, transfer hydrogenation, and related processes. Chemistry. 2013;19:7274-302 pubmed publisher..Also dynamic and oxidative kinetic resolutions leading to chiral alcohols and amines are included. Selected literature reports from early contributions to December 2012 are discussed...
- Fang Z, Wills M. Asymmetric transfer hydrogenation of functionalized acetylenic ketones. J Org Chem. 2013;78:8594-605 pubmed publisher..In several cases, excellent enantioselectivities and yields were achieved. ..
- Friedfeld M, Shevlin M, Hoyt J, Krska S, Tudge M, Chirik P. Cobalt precursors for high-throughput discovery of base metal asymmetric alkene hydrogenation catalysts. Science. 2013;342:1076-80 pubmed publisherAsymmetric hydrogenation of alkenes is one of the most widely used methods for the preparation of single enantiomer compounds, especially in the pharmaceutical and agrochemical industries...
- Chaturvedula V, Prakash I. Hydrogenation of the exocyclic olefinic bond at C-16/C-17 position of ent-kaurane diterpene glycosides of Stevia rebaudiana using various catalysts. Int J Mol Sci. 2013;14:15669-80 pubmed publisherCatalytic hydrogenation of the exocyclic double bond present between C16 and C17 carbons of the four ent-kaurane diterpene glycosides namely rebaudioside A, rebaudioside B, rebaudioside C, and rebaudioside D isolated from Stevia ..
- Morgan J, Morken J. Catalytic enantioselective hydrogenation of vinyl bis(boronates). J Am Chem Soc. 2004;126:15338-9 pubmedCatalytic enantioselective hydrogenation of prochiral vinylmetallic reagents can provide an attractive alternative to hydrometalation and bismetalation of alkenes...
- Li C, Wang C, Villa Marcos B, Xiao J. Chiral counteranion-aided asymmetric hydrogenation of acyclic imines. J Am Chem Soc. 2008;130:14450-1 pubmed publisher..with a chiral phosphate counteranion, a chiral diamine-ligated Ir(III) catalyst displayed excellent enantioselectivities in the asymmetric hydrogenation of a wide range of acyclic imines, affording chiral amines in up to 99% ee.
- Chen Q, Chen M, Yu C, Shi L, Wang D, Yang Y, et al. Biomimetic asymmetric hydrogenation: in situ regenerable Hantzsch esters for asymmetric hydrogenation of benzoxazinones. J Am Chem Soc. 2011;133:16432-5 pubmed publisher..could be regenerated in situ by Ru complexes under hydrogen gas has been employed in the biomimetic asymmetric hydrogenation of benzoxazinones with up to 99% ee in the presence of chiral phosphoric acid...
- Pisani L, Oyama L, Bueno A, Biz C, Albuquerque K, Ribeiro E, et al. Hydrogenated fat intake during pregnancy and lactation modifies serum lipid profile and adipokine mRNA in 21-day-old rats. Nutrition. 2008;24:255-61 pubmed publisher..Ingestion of hydrogenated vegetable fat by the mother during gestation and lactation alters the blood lipid profiles and the expression of proinflammatory adipokynes by the adipose tissue of offspring aged 21 d. ..
- Liu Y, Sandoval C, Yamaguchi Y, Zhang X, Wang Z, Kato K, et al. Hydrogen bonding makes a difference in the rhodium-catalyzed enantioselective hydrogenation using monodentate phosphoramidites. J Am Chem Soc. 2006;128:14212-3 pubmed..moiety was found to display comparable or better efficiency than bisphosphines in the Rh-catalyzed asymmetric hydrogenation of challenging substrates, such as (Z)-methyl alpha-acetoxyacrylate or (E)-beta-aryl itaconate derivatives, ..
- Vega Lopez S, Ausman L, Jalbert S, Erkkilä A, Lichtenstein A. Palm and partially hydrogenated soybean oils adversely alter lipoprotein profiles compared with soybean and canola oils in moderately hyperlipidemic subjects. Am J Clin Nutr. 2006;84:54-62 pubmed..Palm and partially hydrogenated soybean oils, compared with soybean and canola oils, adversely altered the lipoprotein profile in moderately hyperlipidemic subjects without significantly affecting HDL intravascular processing markers. ..
- Hashmi A, Haufe P, Schmid C, Rivas Nass A, Frey W. Asymmetric rhodium-catalyzed hydrogenation meets gold-catalyzed cyclization: Enantioselective synthesis of 8-hydroxytetrahydroisoquinolines. Chemistry. 2006;12:5376-82 pubmed..With very electron-rich furans, instead of the 8-hydroxytetrahydroquinolines as products, furans anellated to seven-membered rings with exocyclic C-C double bonds are formed under the same reaction conditions. ..
- Albuquerque K, Sardinha F, Telles M, Watanabe R, Nascimento C, Tavares do Carmo M, et al. Intake of trans fatty acid-rich hydrogenated fat during pregnancy and lactation inhibits the hypophagic effect of central insulin in the adult offspring. Nutrition. 2006;22:820-9 pubmed..However, the trans group also showed signs of altered appetite signaling mechanisms, suggesting that the early adaptations may have deleterious consequences later in life. ..
- Touge T, Hakamata T, Nara H, Kobayashi T, Sayo N, Saito T, et al. Oxo-tethered ruthenium(II) complex as a bifunctional catalyst for asymmetric transfer hydrogenation and H2 hydrogenation. J Am Chem Soc. 2011;133:14960-3 pubmed publisher..R,R)-1 and their HCl adducts (R,R)-2 exhibited excellent catalytic performance for both asymmetric transfer hydrogenation and the hydrogenation of ketonic substrates under neutral conditions without any cocatalysts to give chiral ..
- Teets T, Cook T, McCarthy B, Nocera D. Redox chemistry, acid reactivity, and hydrogenation reactions of two-electron mixed valence diiridium and dirhodium complexes. Inorg Chem. 2011;50:5223-33 pubmed publisher..3) protonation of 5 with HOTs produces [Rh(2)(I,I)(tfepma)(2)(CN(t)Bu)(3)(?-H)](OTs); and (4) the reversible hydrogenation of 2 proceeds smoothly, furnishing the cis-dihydride complex Ir(2)(II,II)(tfepma)(2)(CN(t)Bu)(2)(H)(2)Cl(2) (..
- Soltani O, Ariger M, Vázquez Villa H, Carreira E. Transfer hydrogenation in water: enantioselective, catalytic reduction of alpha-cyano and alpha-nitro substituted acetophenones. Org Lett. 2010;12:2893-5 pubmed publisherCatalytic reduction of alpha-substituted acetophenones under conditions involving asymmetric transfer hydrogenation in water is described. The reaction is conducted in water and open to air, and formic acid is used as reductant.
- Ohkuma T, Utsumi N, Tsutsumi K, Murata K, Sandoval C, Noyori R. The hydrogenation/transfer hydrogenation network: asymmetric hydrogenation of ketones with chiral eta6-arene/N-Tosylethylenediamine-ruthenium(II) catalysts. J Am Chem Soc. 2006;128:8724-5 pubmedChiral eta6-arene/N-tosylethylenediamine-Ru(II) complexes, known as excellent catalysts for asymmetric transfer hydrogenation of aromatic ketones in basic 2-propanol, can be used for asymmetric hydrogenation using H2 gas...
- Mosley E, Powell G, Riley M, Jenkins T. Microbial biohydrogenation of oleic acid to trans isomers in vitro. J Lipid Res. 2002;43:290-6 pubmed..We concluded that the biohydrogenation of oleic acid by mixed ruminal microbes involves the formation of several positional isomers of trans monoenes rather than only direct biohydrogenation to form stearic acid as previously described. ..
- Yin B, Yang X, Wei G, Ma Y, Wei D. Expression of two old yellow enzyme homologues from Gluconobacter oxydans and identification of their citral hydrogenation abilities. Mol Biotechnol. 2008;38:241-5 pubmed..The results showed that the alpha,beta-double bond of citral cis-isomer 'neral' could be stereoselectively reduced to produce citronellal by the purified OYE homologues...
- Erathodiyil N, Ooi S, Seayad A, Han Y, Lee S, Ying J. Palladium nanoclusters supported on propylurea-modified siliceous mesocellular foam for coupling and hydrogenation reactions. Chemistry. 2008;14:3118-25 pubmed publisher..Pd nanoparticles of 2-3 nm and 4-6 nm were used in reactions involving molecular hydrogen (such as hydrogenation of double bonds and reductive amination), transfer hydrogenation of ketones and epoxides, and coupling ..
- Lichtenstein A, Ausman L, Jalbert S, Schaefer E. Effects of different forms of dietary hydrogenated fats on serum lipoprotein cholesterol levels. N Engl J Med. 1999;340:1933-40 pubmed..Our findings indicate that the consumption of products that are low in trans fatty acids and saturated fat has beneficial effects on serum lipoprotein cholesterol levels. ..
- Faller J, Lavoie A. Enantioselective routes to both enantiomers of aryl alcohols with a single catalyst antipode: Ru and Os transfer hydrogenation catalysts. Org Lett. 2001;3:3703-6 pubmed..In addition, the asymmetric transfer hydrogenation of ketones was investigated with a catalyst, 2, generated in situ from (CyOsCl(2))(2), (1R,2S)-(+)-cis-1-amino-..
- Desai B, Kappe C. Heterogeneous hydrogenation reactions using a continuous flow high pressure device. J Comb Chem. 2005;7:641-3 pubmed
- Balu A, Campelo J, Luque R, Romero A. One-step microwave-assisted asymmetric cyclisation/hydrogenation of citronellal to menthols using supported nanoparticles on mesoporous materials. Org Biomol Chem. 2010;8:2845-9 pubmed publisher..These results constitute the first report of a simple microwave-assisted one-step cyclisation/hydrogenation process for the production of menthols.
- DiRienzo M, Astwood J, Petersen B, Smith K. Effect of substitution of low linolenic acid soybean oil for hydrogenated soybean oil on fatty acid intake. Lipids. 2006;41:149-57 pubmed..No decrease in intake of alpha-linolenic acid was associated with the use of LLSO in place of HSBO because LLSO substitutes for HSBO that are already low in alpha-linolenic acid. ..
- Han S, Leka L, Lichtenstein A, Ausman L, Schaefer E, Meydani S. Effect of hydrogenated and saturated, relative to polyunsaturated, fat on immune and inflammatory responses of adults with moderate hypercholesterolemia. J Lipid Res. 2002;43:445-52 pubmed
- Hu X, Zheng Z. Practical Rh(I)-catalyzed asymmetric hydrogenation of beta-(acylamino)acrylates using a new unsymmetrical hybrid ferrocenylphosphine-phosphoramidite ligand: crucial influence of an N-H proton in the ligand. Org Lett. 2005;7:419-22 pubmed..Excellent enantioselectivities and high turnovers (S/C = 5000) were achieved in the Rh(I)-catalyzed asymmetric hydrogenation of both beta-aryl- and beta-alkyl-beta-(acylamino)acrylates with a new unsymmetrical hybrid ..
- Wasowska I, Maia M, Niedźwiedzka K, Czauderna M, Ribeiro J, Devillard E, et al. Influence of fish oil on ruminal biohydrogenation of C18 unsaturated fatty acids. Br J Nutr. 2006;95:1199-211 pubmed..Neither EPA nor DHA was metabolised by B. fibrisolvens in pure culture. Thus, fish oil inhibits ruminal biohydrogenation by a mechanism which can be interpreted partly, but not entirely, in terms of its effects on B. fibrisolvens...
- de Vries J, Lefort L. The combinatorial approach to asymmetric hydrogenation: phosphoramidite libraries, ruthenacycles, and artificial enzymes. Chemistry. 2006;12:4722-34 pubmed..based on monodentate phosphoramidites enabled the development of an integral HTE protocol for asymmetric hydrogenation. This "instant ligand library" protocol makes it possible to synthesise 96 ligands in one day and ..
- Chen W, Li Y, Yu G, Li C, Zhang S, Zhou Z, et al. Hydrogenation: a simple approach to realize semiconductor-half-metal-metal transition in boron nitride nanoribbons. J Am Chem Soc. 2010;132:1699-705 pubmed publisher..Although the half-metallic property is not robust when the hydrogenation ratio is large, this behavior is sustained for partially hydrogenated zigzag BNNRs with a smaller degree of ..
- Heiden Z, Rauchfuss T. Homogeneous catalytic reduction of dioxygen using transfer hydrogenation catalysts. J Am Chem Soc. 2007;129:14303-10 pubmed..2 +/- 0.2); these values are more disparate than for conventional transfer hydrogenation (Casey, C. P.; Johnson, J. B. J. Org. Chem. 2003, 68, 1998-2001)...
- Rangheard C, de Julián Fernández C, Phua P, Hoorn J, Lefort L, de Vries J. At the frontier between heterogeneous and homogeneous catalysis: hydrogenation of olefins and alkynes with soluble iron nanoparticles. Dalton Trans. 2010;39:8464-71 pubmed publisherThe use of non-supported Fe nanoparticles in the hydrogenation of unsaturated C-C bonds is a green catalytic concept at the frontier between homogeneous and heterogeneous catalysis...
- Mano J, Torii Y, Hayashi S, Takimoto K, Matsui K, Nakamura K, et al. The NADPH:quinone oxidoreductase P1-zeta-crystallin in Arabidopsis catalyzes the alpha,beta-hydrogenation of 2-alkenals: detoxication of the lipid peroxide-derived reactive aldehydes. Plant Cell Physiol. 2002;43:1445-55 pubmed..In the 2-alkenal molecules, P1-ZCr catalyzed the hydrogenation of alpha,beta-unsaturated bonds, but not the reduction of the aldehyde moiety, to produce saturated aldehydes, ..
- Skander M, Humbert N, Collot J, Gradinaru J, Klein G, Loosli A, et al. Artificial metalloenzymes: (strept)avidin as host for enantioselective hydrogenation by achiral biotinylated rhodium-diphosphine complexes. J Am Chem Soc. 2004;126:14411-8 pubmed..7 for avidin (pI = 10.4) and log K(a) = 7.1 for streptavidin (pI = 6.4). It is shown that the optimal operating conditions for the enantioselective reduction are 5 bar at 30 degrees C with a 1% catalyst loading. ..
- DiRienzo M, Lemke S, Petersen B, Smith K. Effect of substitution of high stearic low linolenic acid soybean oil for hydrogenated soybean oil on fatty acid intake. Lipids. 2008;43:451-6 pubmed publisher..Use of HSLL as a substitute for partially hydrogenated soybean oils would result in changes in the fatty acid composition of the US diet consistent with current dietary recommendations. ..
- Eberhardt L, Armspach D, Harrowfield J, Matt D. BINOL-derived phosphoramidites in asymmetric hydrogenation: can the presence of a functionality in the amino group influence the catalytic outcome?. Chem Soc Rev. 2008;37:839-64 pubmed publisher..chiral P(III) ligands turned out to provide high enantioselectivities when used in rhodium-catalysed olefin hydrogenation. The simplest ligand representative of this family is MonoPhos, which can be made straightforwardly from BINOL ..
- Motard Bélanger A, Charest A, Grenier G, Paquin P, Chouinard Y, Lemieux S, et al. Study of the effect of trans fatty acids from ruminants on blood lipids and other risk factors for cardiovascular disease. Am J Clin Nutr. 2008;87:593-9 pubmed
- Bernskoetter W, Lobkovsky E, Chirik P. Kinetics and mechanism of N2 hydrogenation in bis(cyclopentadienyl) zirconium complexes and dinitrogen functionalization by 1,2-addition of a saturated C-H bond. J Am Chem Soc. 2005;127:14051-61 pubmedThe rates of hydrogenation of the N2 ligand in the side-on bound dinitrogen compounds, [(eta(5)-C5Me4H)2Zr]2(mu2,eta(2),eta(2)-N2) and [(eta(5)-C5Me5)(eta(5)-C5H2-1,2-Me2-4-R)Zr]2(mu2,eta(2),eta(2)-N2) (R = Me, Ph), to afford the ..
- Lu J, Dai Y, Jin H, Huang B. Effective increasing of optical absorption and energy conversion efficiency of anatase TiO2 nanocrystals by hydrogenation. Phys Chem Chem Phys. 2011;13:18063-8 pubmed publisherDisorder-engineered nanophase anatase TiO(2) through hydrogenation has been demonstrated to exhibit substantial solar-driven photocatalytic activities [X. Chen, L. Liu, P. Y. Yu, S. S...
- Wienhöfer G, Sorribes I, Boddien A, Westerhaus F, Junge K, Junge H, et al. General and selective iron-catalyzed transfer hydrogenation of nitroarenes without base. J Am Chem Soc. 2011;133:12875-9 pubmed publisher..Notably, the process constitutes a rare example of base-free transfer hydrogenations. ..
- Ito M, Ootsuka T, Watari R, Shiibashi A, Himizu A, Ikariya T. Catalytic hydrogenation of carboxamides and esters by well-defined Cp*Ru complexes bearing a protic amine ligand. J Am Chem Soc. 2011;133:4240-2 pubmed publisherA novel catalytic method for the straightforward hydrogenation of carboxamides and esters to primary alcohols has been developed...
- Willett W, Stampfer M, Manson J, Colditz G, Speizer F, Rosner B, et al. Intake of trans fatty acids and risk of coronary heart disease among women. Lancet. 1993;341:581-5 pubmedTrans isomers of fatty acids, formed by the partial hydrogenation of vegetable oils to produce margarine and vegetable shortening, increase the ratio of plasma low-density-lipoprotein to high-density-lipoprotein cholesterol, so it is ..
- Liu X, Che C. Highly enantioselective synthesis of chiral secondary amines by gold(I)/chiral Brønsted acid catalyzed tandem intermolecular hydroamination and transfer hydrogenation reactions. Org Lett. 2009;11:4204-7 pubmed publisher..enriched secondary amines with excellent ee values through the tandem intermolecular hydroamination/transfer hydrogenation of alkynes using a "gold(I) complex-chiral Brønsted acid" protocol is developed...
- Moran W, Morken J. Rh-catalyzed enantioselective hydrogenation of vinyl boronates for the construction of secondary boronic esters. Org Lett. 2006;8:2413-5 pubmedreaction: see text] Rh-catalyzed hydrogenation of prochiral vinyl boronates occurs in an enantioselective fashion in the presence of the chiral ligand Walphos 1...
- Greiner L, Laue S, Liese A, Wandrey C. Continuous homogeneous asymmetric transfer hydrogenation of ketones: lessons from kinetics. Chemistry. 2006;12:1818-23 pubmed..Polymer enlargement allowed the continuous operation of transfer hydrogenation in a chemical membrane reactor with total turnover numbers of up to 2.6 x 10(3) and a space-time yield of 0...
- Hambraeus G, Nyberg N. Enzymatic hydrogenation of trans-2-nonenal in barley. J Agric Food Chem. 2005;53:8714-21 pubmed..The possibility to enhance ALH1 activity in planta is discussed--not only with respect to the physiological consequences thereof--but also in relation to improved beer quality. ..
- Kairenius P, Toivonen V, Shingfield K. Identification and ruminal outflow of long-chain fatty acid biohydrogenation intermediates in cows fed diets containing fish oil. Lipids. 2011;46:587-606 pubmed publisher..in cows fed the Control and FO treatments suggests that the first committed steps of 20:5n-3, 21:5n-3 and 22:6n-3 hydrogenation in the rumen involve the reduction and/or isomerisation of double bonds closest to the carboxyl group.
- Soni R, Cheung F, Clarkson G, Martins J, Graham M, Wills M. The importance of the N-H bond in Ru/TsDPEN complexes for asymmetric transfer hydrogenation of ketones and imines. Org Biomol Chem. 2011;9:3290-4 pubmed publisher..containing two alkyl groups on the non-tosylated nitrogen atom are poor catalysts for asymmetric transfer hydrogenation of ketones and imines; this observation provides direct evidence for the importance of the N-H interaction in ..
- Zhang W, Zhang X. Highly enantioselective hydrogenation of alpha-dehydroamino esters and itaconates with triphosphorous bidentate ligands and the unprecedented solvent effect thereof. J Org Chem. 2007;72:1020-3 pubmed..4% ee) in Rh-catalyzed hydrogenation of alpha-dehydroamino esters in acetone...
- Morgado N, Sanhueza J, Nieto S, Valenzuela A. Effect of the degree of hydrogenation of fish oil on the enzymatic activity and on the fatty acid composition of hepatic microsomes from young and aged rats. Ann Nutr Metab. 2003;47:124-31 pubmedBy modifying the degree of hydrogenation of dietary fat, it is possible to modify the fatty acid composition and the biochemical activity of cellular tissues. The age can be another variable influencing these modifications...
- Shibahara F, Bower J, Krische M. Diene hydroacylation from the alcohol or aldehyde oxidation level via ruthenium-catalyzed C-C bond-forming transfer hydrogenation: synthesis of beta,gamma-unsaturated ketones. J Am Chem Soc. 2008;130:14120-2 pubmed publisherUnder the conditions of ruthenium-catalyzed transfer hydrogenation, isoprene couples to benzylic and aliphatic alcohols 1a-g to deliver beta,gamma-unsaturated ketones 3a-g in good to excellent isolated yields...