Colloidal palladium nanoparticles with in situ H2: Reducing system for ,-unsaturated carbonyl compounds

Synthetic Communications

Volumn 39, Issue 19, 2009, Pages 3509-3520

  De Castro, Kathlia A ^a   Oh, Seungchan ^a   Yun, Jongchan ^a   Lim, Jin Kyu ^a   An, Gwangil ^b   Kim, Dong Kook ^a   Rhee, Hakjune ^a  

^a Hanyang University   (South Korea)

^b Korea Institute of Radiation and Medical Science   (South Korea)

Author keywords

, unsaturated carbonyl compounds; Hydride; Hydrogenation; Palladium nano sized particle; Saturated alcohol

Indexed keywords

1 (4 METHOXY PHENYL) 3 PHENYL 1 PROPANOL; 1 METHOXY 4 (3 PHENYLPROPYL)BENZENE; 1,3 DIPHENYL 1 PROPANOL; 1,3 DIPHENYLPROPANE; 2 BENZYL 1 HEPTANOL; 2 BENZYL 1 OCTANOL; 2 METHYL 3 PHENYL 1 PROPANOL; 2 PENTYL 2 CYCLOPENTANOL; 2,4 DIETHYL 1 HEPTANOL; 3 (4 METHOXY PHENYL) 1 PHENYL 1 PROPANOL; 3 PHENYL 1 PROPANOL; 3,7 DIMETHYL 1 OCTANOL; 4 PHENYL 2 BUTANOL; CARBONYL DERIVATIVE; HEPTANOL; HEXANOL; METHANOL; NANOPARTICLE; PALLADIUM; PENTANOL DERIVATIVE; PROPRANOLOL DERIVATIVE; UNCLASSIFIED DRUG; UNDECANOL;

ARTICLE; CHEMICAL REACTION; COLLOID; REDUCTION;

EID: 70349435008     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902788117     Document Type: Article

References (40)

1. Petrier, C.; Luche, J. L. Ultrasonically improved reductive properties of an aqueous zinc-nickel dichloride system, 1: Selective reduction of a,b-unsaturated carbonyl compounds. Tetrahedron Lett. 1987, 28, 2347
2. Shibata, M.; Kiwata, N.; Masumoto, T.; Kimura, H. Selective hydrogenation of unsaturated carbonyl compounds over an oxidized gold-zirconium alloy. J. Chem. Soc, Chem. Commun. 1988, 154
3. Bianchini, C; Farnetti, E.; Graziani, M.; Peruzzini, M.; Polo, A. Chemoselective hydrogen-transfer reduction of a,P-unsaturated ketones catalyzed by isostructural iron(II), ruthenium(II), and osmium(II) cis-hydride (r)-dihydrogen) complexes. Orga-nometallics 1993, 12, 3753
4. Fraga, B. M.; Gonazalez, P.; Guillermo, R.; Hernandez, M. G. A study of the microbiological reduction of a,P-unsaturated carbonyl ent-kaurenes by Gibberella fujikuroi. Tetrahedron 1996, 52, 13767
5. Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Meneses, R.; Romera, J. L. Raney nickel: An effective reagent for reductive dehalogenation of organic halides. Synlett 2001, 485
6. 4NH-K N,k P)]. J. Organomet. Chem. 2000, 616, 19
7. Chen, J.; Daeuble, J. F.; Stryker, J. M. Phosphine effects in the copper(I) hydride-catalyzed hydrogenation of ketones and regioselective 1,2-reduction of a,P-unsaturated ketones and aldehydes: Hydrogenation of decalin and steroidal ketones and enones. Tetrahedron 2000, 56, 2789
8. Noyori, R.; Yamakawa, M.; Hashiguchi, S. Metal-ligand bifunctional catalysis: A non-classical mechanism for asymmetric hydrogen transfer between alcohols and carbonyl compounds. J. Org. Chem. 2001, 66, 7931
9. Sakaguchi, S.; Yamaga, T.; Ishii, Y. Iridium-catalyzed transfer hydrogenation of a,P-unsa-turated and saturated carbonyl compounds with 2-propanol. J. Org. Chem. 2001, 66, 4710
10. Selvam, P.; Sonavane, S. U.; Mohaptra, S. K.; Jayaram, R. V. Chemoselective reduction of a,P-unsaturated carbonyls over novel mesoporous CoHMA molecular sieves under hydrogen transfer conditions. Adv. Synth. Catal. 2004, 346, 542
11. Sonavane, S. U.; Jayaram, R. V. Selective reduction of C=O in a,P-unsaturated carbonyls through catalytic hydrogen transfer reaction over mixed metal oxides. Synlett 2004, 1, 146.
12. Johnson, M. R.; Rickborn, B. Sodium borohydride reduction of conjugated aldehydes and ketones. J. Org. Chem. 1970, 35, 1041
13. Mahoney, W. S.; Stryker, J. M. Hydride-mediated homogeneous catalysis: Catalytic reduction of a,P-unsa-turated ketones using [(Ph3P)CuH]6 and H2. J. Am Chem. Soc. 1989, 111, 8818
14. Handique, J. G.; Purkayashtha, A.; Baruah, J. B. Reduction of a,P-unsatu-rated carbonyl compounds by Ni2+-BH4~. J. Organomet. Chem. 2001, 620, 90.
15. Ranu, B. C; Samanta, S. Reduction of activated conjugated alkenes by the InCl3-NaBH4 reagent system. Tetrahedron 2003, 59, 7901.
16. Mori, A.; Misuzaki, T.; Miyakawa, Y.; Ohashi, E.; Haga, T.; Maegawa, T.; Monguchi, Y.; Sajiki, H. Chemoselective hydrogenation method catalyzed by Pd/C using diphenylsulfide as a reasonable catalyst poison. Tetrahedron 2006, 62, 11925.
17. Kralik, M.; Biffis, A. Catalysis by metal nanoparticles supported on functional organic polymers. J. Mol. Catal A: Chem. 2001, 177, 113
18. Moreno-Manas, M.; Pleixats, R. Formation of carbon-carbon bonds under catalysis by transition-metal nanoparticles. Acc. Chem. Res. 2003, 36, 638
19. Reetz, M. T.; de Vries, J. G. Ligand-free Heck reactions using low Pd-loading. Chem. Commun. 2004, 1559
20. Astruc, D.; Lu, F.; Aranzaes, J. R. Nanoparticles as recyclable catalysts. The frontier between homogeneous and heterogeneous catalysis. Angew. Chem. Int. Ed. 2005, 44, 7852
21. Alonso, F.; Osante, I.; Yus, M. Conjugate reduction of a,b-unsaturated carbonyl compounds promoted by nickel nanoparticles. Synlett 2006, 18, 3017
22. Thiery, E.; Le Bras, J.; Muzart, J. Palladium nanoparticles-catalyzed regio-and chemoselective hydrogenolysis of benzylic epoxides in water. Green Chem. 2007, 9, 326.
23. de Vries, A. H. M.; Mulders, J. M. C. A.; Mommers, J. H. M.; Henderickx, H. J. W.; de Vries, J. G. Homeopathic ligand-free palladium as a catalyst in the Heck reaction: A comparison with palladacycle. Org. Lett. 2003, 5, 3285
24. Pryjomska-Ray, I.; Gniewek, A.; Trzeciak, A. M.; Ziołkowski, J. J.; Tylus, W. Homogeneous/heterogeneous palladium-based catalytic system for Heck reaction: The reversible transfer of palladium between solution and support. Top. Catal. 2006, 40, 173
25. Astruc, D. Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon-carbon coupling precatalysts: A unifying view. Inorg. Chem. 2007, 46, 1884
26. Zhu, Y.; Peng, S. C; Emi, A.; Su, Z.; Monalisa; Kemp, R. A. Supported ultrasmall palladium on magnetic nanoparticles used as catalysts for Suzuki cross-coupling and Heck reactions. Adv. Synth. Catal. 2007, 349, 1917.
27. Yoon, B.; Kim, H.; Wai, C. M. Dispersing palladium nanoparticles using a water-in-oil microemulsion-homogenization of heterogeneous catalysis. Chem. Commun. 2003, 1040
28. Nakao, R.; Rhee, H.; Uozumi, Y. Hydrogenation and dehalogenation under aqueous conditions with an amphiphilic-polymer-supported nanopalladium catalyst. Org. Lett. 2005, 7, 163
29. Divakar, D.; Manikandan, D.; Rupa, V.; Preethi, E. L.; Chandrasekar, R.; Sivakumar, T. Palladium-nanoparticle intercalated vermi-culite for selective hydrogenation of a,b-unsaturated aldehydes. J. Chem. Technol. Biotechnol. 2007, 82, 253.
30. Illa, O.; Rodr?iquez-Garc?ia, C; Acosta-Silva, C; Favier, I.; Picurelli, D.; Oliva, A.; Gomez, M.; Branchadell, V.; Ortuno, R. M. Cyclopropanation of cyclohexenone by diazomethane catalyzed by palladium diacetate: Evidence for the formation of palladium(0) nanoparticles. Organometallics 2007, 26, 3306.
31. Pitts, M. R.; Harrison, J. R.; Moody, C. J. Indium metal as reducing agent in organic synthesis. J. Chem. Soc, Perkin Trans. 1 2001, 955
32. Ranu, B. C; Dutta, J.; Guchhait, S. K. Indium metal as a reducing agent: Selective reduction of the carbon-carbon double bond in highly activated conjugated alkenes. Org. Lett. 2001, 3, 2603.
33. Arjona, O.; Perez-Ossorio, R.; Perez-Rubalcaba, A.; Quiroga, M. L. Stereochemistry of addition to the carbonyl group, part 17: Study of the factors affecting asymmetric induction in condensation reactions of methyl-and phenylmagnesium bromide with chiral carbonyl compounds. J. Chem. Soc. Perkin Trans 2: Phys. Org. Chem. 1981, 4, 597.
34. Schmitt, K. D. Two-tailed surfactants having one aromatic containing tail and their use in chemical waterflooding. US Patent 4517128 A, 1985.
35. Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; De Nino, A.; Sambri, L.; Tagarelli, A. Allyl alcohols and organocerium reagents, II: Mechanism and extensibility of the reaction. Eur. J. Org. Chem. 2000, 1, 99.
36. Rochat, S.; Minardi, C.; De Saint Laumer, J.; Herrmann, A. Controlled release of perfumery aldehydes and ketones by Norrish type-II photofrag-mentation of a-keto esters in undegassed solution. Helv. Chim. Acta 2000, 83, 1645.
37. Qin, C.; Wu, H.; Cheng, J.; Chen, X.; Liu, M.; Zhang, W.; Su, W.; Ding, J. The palladium-catalyzed addition of aryl-and heteroarylboronic acids to aldehydes. J. Org. Chem. 2007, 72, 4102.
38. Sajiki, H.; Aoki, F.; Esaki, H.; Maegawa, T.; Hirota, K. Efficient C-H=C-D exchange reaction on the alkyl side chain of aromatic compounds using heterogeneous Pd=C in D2O. Org. Lett. 2004, 6, 1485.
39. Khurana, J. M.; Kiran, D. Rapid reduction of chalcones to tetrahydrochal-cones using nickel boride. J. Chem. Res. 2006, 6, 374.
40. Jacquesy, J. C.; Coustard, J. M.; Jouannetaud, M. P. Trapping of protonated phenols (ethers) by aromatics in super acids. Top. Catal. 1998, 6, 1.