메뉴 건너뛰기




Volumn 43, Issue 5, 2013, Pages 656-667

HAP-Pd(0): A highly efficient recyclable heterogeneous catalyst for the selective reduction of carbon-carbon double bond in ,-unsaturated ketones

Author keywords

, unsaturated ketones; HAP Pd(0); heterogeneous catalysis; reductions; selectivity

Indexed keywords

ACETONITRILE; AMMONIUM FORMATE; CARBON; HYDROGEN; HYDROXYAPATITE; KETONE DERIVATIVE; PALLADIUM;

EID: 84869481757     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.605242     Document Type: Article
Times cited : (15)

References (43)
  • 3
    • 0001726068 scopus 로고
    • Influence of Ru precursor, support, and solvent in the hydrogenation of citral over ruthenium catalysts
    • Neri, G.; Mercadante, L.; Donato, A.; Visco, A.; Galvagno, S. Influence of Ru precursor, support, and solvent in the hydrogenation of citral over ruthenium catalysts. Catal. Lett. 1994, 29, 379-386.
    • (1994) Catal. Lett , vol.29 , pp. 379-386
    • Neri, G.1    Mercadante, L.2    Donato, A.3    Visco, A.4    Galvagno, S.5
  • 4
    • 33846231812 scopus 로고
    • Chemioselectivity in cinnamaldehyde hydrogenation induced by shape selectivity effects in Pt-Y zeolite catalysts
    • Gallezot, P.; Giroir-Fendler, A.; Richard, D. Chemioselectivity in cinnamaldehyde hydrogenation induced by shape selectivity effects in Pt-Y zeolite catalysts. Catal. Lett. 1990, 5, 169-174.
    • (1990) Catal. Lett , vol.5 , pp. 169-174
    • Gallezot, P.1    Giroir-Fendler, A.2    Richard, D.3
  • 5
    • 0002157183 scopus 로고    scopus 로고
    • Structure sensitivity of the hydrogenation of crotonaldehyde over Pt=SiO2 and Pt=TiO2
    • Englisch, M.; Jentys, A.; Lercher, J. A. Structure sensitivity of the hydrogenation of crotonaldehyde over Pt=SiO2 and Pt=TiO2. J. Catal. 1997, 166, 25-35.
    • (1997) J. Catal , vol.166 , pp. 25-35
    • Englisch, M.1    Jentys, A.2    Lercher, J.A.3
  • 6
    • 2342598421 scopus 로고    scopus 로고
    • Selective hydrogenation of-a,b-unsaturated aldehydes and other C=O and C=C bonds containing compounds
    • Claus, P. Selective hydrogenation of-a,b-unsaturated aldehydes and other C=O and C=C bonds containing compounds. Top. Catal. 1998, 5, 51-62.
    • (1998) Top. Catal , vol.5 , pp. 51-62
    • Claus, P.1
  • 7
    • 0009374205 scopus 로고
    • Catalytic transfer hydrogenation
    • Brieger,G. B.; Nestrick, T. J. Catalytic transfer hydrogenation. Chem. Rev. 1974, 74, 567-580.
    • (1974) Chem. Rev , vol.74 , pp. 567-580
    • Briegerg, B.1    Nestrick, T.J.2
  • 8
    • 33845378909 scopus 로고
    • Heterogeneous catalytic transfer hydrogenation and its relation to other methods for reduction of organic compounds
    • Jonstone, R. A.; Wilby, W. A. H.; Entwistle, I. D. Heterogeneous catalytic transfer hydrogenation and its relation to other methods for reduction of organic compounds. Chem. Rev. 1985, 85, 129-180.
    • (1985) Chem. Rev , vol.85 , pp. 129-180
    • Jonstone, R.A.1    Wilby, W.A.H.2    Entwistle, I.D.3
  • 9
    • 37049088636 scopus 로고
    • Ruthenium-catalysed transfer hydrogenation of imines by propan-2-ol
    • Wang, G. Z.; Backvall, J. E. Ruthenium-catalysed transfer hydrogenation of imines by propan-2-ol. J. Chem. Soc., Chem. Commun. 1992, 14, 980-981.
    • (1992) J. Chem. Soc Chem. Commun , vol.14 , pp. 980-981
    • Wang, G.Z.1    Backvall, J.E.2
  • 10
    • 0037474679 scopus 로고    scopus 로고
    • 2O
    • DOI 10.1016/S0040-4039(03)00462-3
    • Lee, H.; An, M. Selective 1,4-reduction of unsaturated carbonyl compounds using Co2(CO)8-H2O. Tetrahedron Lett. 2003, 44, 2775-2778. (Pubitemid 36324377)
    • (2003) Tetrahedron Letters , vol.44 , Issue.14 , pp. 2775-2778
    • Lee, H.-Y.1    An, M.2
  • 11
    • 0035967759 scopus 로고    scopus 로고
    • Iridium-catalyzed transfer hydrogenation of α,β-unsaturated and saturated carbonyl compounds with 2-propanol
    • DOI 10.1021/jo0156722
    • Sakaguchi, S.; Yamaga, T.; Ishii, T. Y. Iridium-catalyzed transfer hydrogenation of a,bunsaturated and saturated carbonyl compounds with 2-propanol. J. Org. Chem. 2001, 66, 4710-4712. (Pubitemid 32861853)
    • (2001) Journal of Organic Chemistry , vol.66 , Issue.13 , pp. 4710-4712
    • Sakaguchi, S.1    Yamaga, T.2    Ishii, Y.3
  • 12
    • 0033578743 scopus 로고    scopus 로고
    • Rhodium-catalyzed reduction of esters to alcohols using diphenylsilane
    • DOI 10.1016/S0040-4039(99)01435-5, PII S0040403999014355
    • Ohta, T.; Kamiya, M.; Kusui, K.; Michibata, T.; Nobutomo, M.; Furukawa, I. Rhodiumcatalyzed reduction of esters to alcohols using diphenylsilane. Tetrahedron Lett. 1999, 40, 6963-6966. (Pubitemid 29429569)
    • (1999) Tetrahedron Letters , vol.40 , Issue.38 , pp. 6963-6966
    • Ohta, T.1    Kamiya, M.2    Kusui, K.3    Michibata, T.4    Nobutomo, M.5    Furukawa, I.6
  • 13
    • 54249159627 scopus 로고    scopus 로고
    • Enhanced activity for oxygen reduction reaction on "pt3co" nanoparticles: Direct evidence of percolated and sandwich-segregation structures
    • Chen, S.; Ferreira, P. J.; Sheng, W.; Yubuuchi, N.; Lawrence, F. A.; Shao-Horn, Y. Enhanced activity for oxygen reduction reaction on "Pt3Co" nanoparticles: Direct evidence of percolated and sandwich-segregation structures. J. Am. Chem. Soc. 2008, 130, 13818-13819.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 13818-13819
    • Chen, S.1    Ferreira, P.J.2    Sheng, W.3    Yubuuchi, N.4    Lawrence, F.A.5    Shao-Horn, Y.6
  • 14
    • 63449083669 scopus 로고    scopus 로고
    • Reduction of N2O by H2 catalyzed by platinum monocation: A theoretical study
    • Li, T. H.; Wang, C. M.; Yu, S. W.; Liu, X. Y.; Fu, H.; Xie, X. G. Reduction of N2O by H2 catalyzed by platinum monocation: A theoretical study. J. Mol. Str.: Theochem. 2009, 902, 109-113.
    • (2009) J. Mol. Str.: Theochem , vol.902 , pp. 109-113
    • Li, T.H.1    Wang, C.M.2    Yu, S.W.3    Liu, X.Y.4    Fu, H.5    Xie, X.G.6
  • 15
    • 1842478923 scopus 로고    scopus 로고
    • Chemoselective Reduction of α,βUnsaturated Aldehydes, Ketones, Carboxylic Acids, and Esters with Nickel Boride in Methanol-Water
    • DOI 10.1246/bcsj.77.549
    • Khurana, J. M.; Sharma, P. Chemoselective reduction of a,b-unsaturated aldehydes, ketones, carboxylic acids, and esters with nickel boride in methanol-water. Bull. Chem. Soc. Japan 2004, 77, 549-552. (Pubitemid 38436396)
    • (2004) Bulletin of the Chemical Society of Japan , vol.77 , Issue.3 , pp. 549-552
    • Khurana, J.M.1    Sharma, P.2
  • 16
    • 0242710938 scopus 로고    scopus 로고
    • Catalytic transfer reduction of conjugated alkenes and an imine using polymer-supported formates
    • DOI 10.1016/j.tetlet.2003.10.019
    • Basu, B.; Bhuiyan, M. M. H.; Das, P.; Hossain, I. Catalytic transfer reduction of conjugated alkenes and an imine using polymer-supported formates. Tetrahedron Lett. 2003, 44, 8931-8934. (Pubitemid 37412429)
    • (2003) Tetrahedron Letters , vol.44 , Issue.50 , pp. 8931-8934
    • Basu, B.1    Bhuiyan, Md.M.H.2    Das, P.3    Hossain, I.4
  • 17
    • 45449087505 scopus 로고    scopus 로고
    • Reduction of a,b-unsaturated carbonyl compounds by palladium(II) and nickel(II) complexes having nitrogen-containing ligands
    • Jana, P. P.; Sarma, R.; Baruah, J. B. Reduction of a,b-unsaturated carbonyl compounds by palladium(II) and nickel(II) complexes having nitrogen-containing ligands. J. Mol. Catal. A: Chem. 2008, 289, 57-60.
    • (2008) J. Mol. Catal. A: Chem , vol.289 , pp. 57-60
    • Jana, P.P.1    Sarma, R.2    Baruah, J.B.3
  • 18
    • 22844432721 scopus 로고    scopus 로고
    • Palladium-catalyzed simple and efficient hydrogenative cleavage of azo compounds using recyclable polymer-supported formate
    • DOI 10.1139/v05-071
    • Keelara, A.; Srinivasa, G. S.; Gowda, D. C. Palladium-catalyzed simple and efficient hydrogenative cleavage of azo compounds using recyclable polymer-supported formate. Can. J. Chem. 2005, 83, 517-520. (Pubitemid 41039298)
    • (2005) Canadian Journal of Chemistry , vol.83 , Issue.5 , pp. 517-520
    • Abiraj, K.1    Srinivasa, G.R.2    Gowda, D.C.3
  • 19
    • 51849124678 scopus 로고    scopus 로고
    • Palladium=carboncatalyzed hydrogen transfer reactions using magnesium=water as hydrogen donor
    • Muhammad, O.; Sonavane, S. U.; Sasson, Y.; Chidambaram, M. Palladium=carboncatalyzed hydrogen transfer reactions using magnesium=water as hydrogen donor. Catal. Lett. 2008, 125, 46-51.
    • (2008) Catal. Lett , vol.125 , pp. 46-51
    • Muhammad, O.1    Sonavane, S.U.2    Sasson, Y.3    Chidambaram, M.4
  • 20
    • 0027439715 scopus 로고
    • Mild reduction of a,b-unsaturated ketones and aldehydes with an oxygen-activated palladium catalyst
    • Sommovigo, M.; Alper, H. Mild reduction of a,b-unsaturated ketones and aldehydes with an oxygen-activated palladium catalyst. Tetrahedron Lett. 1993, 34, 59-62.
    • (1993) Tetrahedron Lett , vol.34 , pp. 59-62
    • Sommovigo, M.1    Alper, H.2
  • 21
    • 0005422495 scopus 로고
    • Palladium-catalyzed hydrogenation of a,b-unsaturated sulfones and phosphonates
    • Cho, I. S.; Yamaga, T.; Ishii, Y. Palladium-catalyzed hydrogenation of a,b-unsaturated sulfones and phosphonates. J. Org. Chem. 1994, 59, 4027-4028.
    • (1994) J. Org. Chem , vol.59 , pp. 4027-4028
    • Cho, I.S.1    Yamaga, T.2    Ishii, Y.3
  • 22
    • 34848913444 scopus 로고    scopus 로고
    • Palladium catalyzed mild reduction of α,β-unsaturated compounds by triethylsilane
    • DOI 10.1016/j.jorganchem.2007.08.017, PII S0022328X07006080
    • Mirza-Aghayan, M.; Boukherroub, R.; Bolourtchian, M.; Rahimifard, M. Palladiumcatalyzed mild reduction of a,b-unsaturated compounds by triethylsilane. J. Organometal. Chem. 2007, 692, 5113-5116. (Pubitemid 47513734)
    • (2007) Journal of Organometallic Chemistry , vol.692 , Issue.23 , pp. 5113-5116
    • Mirza-Aghayan, M.1    Boukherroub, R.2    Bolourtchian, M.3    Rahimifard, M.4
  • 23
    • 33846893890 scopus 로고    scopus 로고
    • Carbon-carbon coupling reactions catalyzed by heterogeneous palladium catalysts
    • and references cited therein
    • Yin, L.; Liebscher, J. Carbon-carbon coupling reactions catalyzed by heterogeneous palladium catalysts. Chem. Rev. 2007, 107, 133, and references cited therein.
    • (2007) Chem. Rev , vol.107 , pp. 133
    • Yin, L.1    Liebscher, J.2
  • 24
    • 79954606760 scopus 로고    scopus 로고
    • Nanosized Mn(acac 3 anchored on amino-functionalized silica for the selective oxidative synthesis of 2-arylbenzimidazoles, 2-arylbenzothiazoles, and aerobic oxidation of benzoins in water
    • Sodhi, R. K.; Paul, S. Nanosized Mn(acac)3 anchored on amino-functionalized silica for the selective oxidative synthesis of 2-arylbenzimidazoles, 2-arylbenzothiazoles, and aerobic oxidation of benzoins in water. Catal. Lett. 2011, 141, 608-615.
    • (2011) Catal. Lett , vol.141 , pp. 608-615
    • Sodhi, R.K.1    Paul, S.2
  • 26
    • 33646587365 scopus 로고    scopus 로고
    • Catalytic properties of several palladium complexes covalently anchored onto silica for the aerobic oxidation of alcohols
    • Choudhary, D.; Paul, S.; Gupta, R.; Clark, J. H. Catalytic properties of several palladium complexes covalently anchored onto silica for the aerobic oxidation of alcohols. Green Chem. 2006, 8, 479-482, and references cited therein.
    • (2006) Green Chem , vol.8 , pp. 479-482
    • Choudhary, D.1    Paul, S.2    Gupta, R.3    Clark, J.H.4
  • 27
    • 50249106495 scopus 로고    scopus 로고
    • Hydroxyapatite-supported palladium(0) as a highly efficient catalyst for the Suzuki coupling and aerobic oxidation of benzyl alcohols in water
    • Jamwal, N.; Gupta, M.; Paul, S. Hydroxyapatite-supported palladium (0) as a highly efficient catalyst for the Suzuki coupling and aerobic oxidation of benzyl alcohols in water. Green Chem. 2008, 10, 999-1003.
    • (2008) Green Chem , Issue.10 , pp. 999-1003
    • Jamwal, N.1    Gupta, M.2    Paul, S.3
  • 28
    • 62649116394 scopus 로고    scopus 로고
    • The oxidative aromatization of Hantzsch 1,4-dihydropyridines by molecular oxygen using surface functionalized silica-supported cobalt catalysts
    • Shamim, T.; Gupta, M.; Paul, S. The oxidative aromatization of Hantzsch 1,4-dihydropyridines by molecular oxygen using surface functionalized silica-supported cobalt catalysts. J. Mol. Catal. A: Chem. 2009, 302, 15-19.
    • (2009) J. Mol. Catal. A: Chem , vol.302 , pp. 15-19
    • Shamim, T.1    Gupta, M.2    Paul, S.3
  • 29
    • 85004724143 scopus 로고
    • Ammonium formate in organic synthesis a versatile agent in catalytic hydrogen transfer reductions
    • Ram, S.; Ehrenkaufer, R. E. Ammonium formate in organic synthesis: A versatile agent in catalytic hydrogen transfer reductions. Synthesis 1988, 91-94.
    • (1988) Synthesis , pp. 91-94
    • Ram, S.1    Ehrenkaufer, R.E.2
  • 30
    • 0000062612 scopus 로고
    • A novel application of ammonium formate=palladium on carbon for selective reduction of the heterocyclic ring in quinolines and isoquinolines
    • Balczewski, P.; Joule, J. A. A novel application of ammonium formate=palladium on carbon for selective reduction of the heterocyclic ring in quinolines and isoquinolines. Synth. Commun. 1990, 20, 2815-2819.
    • (1990) Synth. Commun , vol.20 , pp. 2815-2819
    • Balczewski, P.1    Joule, J.A.2
  • 31
    • 0025756818 scopus 로고
    • A new convenient reduction of aralkyl ketones to alcohols using Raney nickel-ammonium formate
    • Chem, F.-E.; Zhang, H.; Yuan, W.; Zhang, W.-W. A new convenient reduction of aralkyl ketones to alcohols using Raney nickel-ammonium formate. Synth. Commun. 1991, 21, 107-109.
    • (1991) Synth. Commun , vol.21 , pp. 107-109
    • Chem, F.-E.1    Zhang, H.2    Yuan, W.3    Zhang, W.-W.4
  • 32
    • 0003133973 scopus 로고
    • Regioselective hydrogenolysis of benzyl glycosides
    • Bieg, T.; Szeja, W. Regioselective hydrogenolysis of benzyl glycosides. Carbohydr. Res. 1990, 205, c10-c11.
    • (1990) Carbohydr. Res , vol.205
    • Bieg, T.1    Szeja, W.2
  • 33
    • 0025988227 scopus 로고
    • A useful methodology for the regioselective deprotection of 1,3-dibenzyluracils
    • Botta, M.; Summa, V.; Saladino, R.; Nicoletti, R. A useful methodology for the regioselective deprotection of 1,3-dibenzyluracils. Synth. Commun. 1991, 21, 2181-2187.
    • (1991) Synth. Commun , vol.21 , pp. 2181-2187
    • Botta, M.1    Summa, V.2    Saladino, R.3    Nicoletti, R.4
  • 34
    • 84972934488 scopus 로고
    • Oximes from conjugated nitroalkanes using Pd=C ammonium formate
    • Kabalka, G. W.; Pace, R. D.; Wadgonkar, P. P. Oximes from conjugated nitroalkanes using Pd=C ammonium formate. Synth. Commun. 1990, 20, 2453-2458.
    • (1990) Synth. Commun , vol.20 , pp. 2453-2458
    • Kabalka, G.W.1    Pace, R.D.2    Wadgonkar, P.P.3
  • 35
    • 0028097980 scopus 로고
    • Palladium assisted transfer hydrogenation of cyclic α,β- unsaturated ketones by ammonium formate
    • DOI 10.1016/0040-4039(94)88193-6
    • Rao, H. S. P.; Reddy, S. Palladium-assisted transfer hydrogenation of cyclic a,bunsaturated ketones by ammonium formate. Tetrahedron Lett. 1994, 35, 171-174. (Pubitemid 24046149)
    • (1994) Tetrahedron Letters , vol.35 , Issue.1 , pp. 171-174
    • Rao, H.S.P.1    Reddy, K.S.2
  • 36
    • 1342332861 scopus 로고    scopus 로고
    • Pd-catalyzed completely selective hydrogenation of conjugated and isolated C=C of citral (3,7-dimethyl-2, 6-octadienal) in supercritical carbon dioxide
    • Chatterjee, M.; Chatterjee, A.; Ikushima, Y. Pd-catalyzed completely selective hydrogenation of conjugated and isolated C=C of citral (3,7-dimethyl-2,6-octadienal) in supercritical carbon dioxide. Green Chem. 2004, 6, 114-118. (Pubitemid 38253320)
    • (2004) Green Chemistry , vol.6 , Issue.2 , pp. 114-118
    • Chatterjee, M.1    Chatterjee, A.2    Ikushima, Y.3
  • 37
    • 33845312957 scopus 로고    scopus 로고
    • Palladium nanoparticles in polymers: Catalyst for alkene hydrogenation, carbon-carbon cross-coupling reactions, and aerobic alcohol oxidation
    • DOI 10.1055/s-2006-950329
    • Park, C. M.; Kwon, M. S.; Park, J. Palladium nanoparticles in polymers: Catalysts for alkene hydrogenation carbon-carbon cross coupling reactions and aerobic alcohol oxidation. Synthesis 2006, 3790-3794. (Pubitemid 44870874)
    • (2006) Synthesis , Issue.22 , pp. 3790-3794
    • Cheon, M.P.1    Min, S.K.2    Park, J.3
  • 38
    • 33749521300 scopus 로고    scopus 로고
    • Transesterifications catalysed by solid, reusable apatite-zinc chloride catalysts
    • DOI 10.1039/b605835n
    • Solhy, A.; Clark, J. H.; Tahir, R.; Sebti, S.; Larzek, M. Trans-esterifications catalysed by solid, reusable apatite-zinc chloride catalysts. Green Chem. 2006, 8, 871-874. (Pubitemid 44527089)
    • (2006) Green Chemistry , vol.8 , Issue.10 , pp. 871-874
    • Solhy, A.1    Clark, J.H.2    Tahir, R.3    Sebti, S.4    Larzek, M.5
  • 39
    • 4544377758 scopus 로고    scopus 로고
    • 2O catalyzed by selenium under atmospheric pressure
    • DOI 10.1055/s-2004-830871
    • Tian, F.; Lu, S. Selective reduction of a,b-unsaturated carbonyl compounds with CO= H2O catalyzed by selenium under atmospheric pressure. Synlett 2004, 1953-1956. (Pubitemid 39222891)
    • (2004) Synlett , Issue.11 , pp. 1953-1956
    • Tian, F.1    Lu, S.2
  • 40
    • 33645996357 scopus 로고    scopus 로고
    • Catalytic transfer reduction of electron-deficient alkenes and an imine using potassium formate and catalytic palladium acetate
    • Bhuiyan, M. M. H. Catalytic transfer reduction of electron-deficient alkenes and an imine using potassium formate and catalytic palladium acetate. Pak. J. Sci. Ind. Res. 2005, 48, 377-380.
    • (2005) Pak. J. Sci. Ind. Res , vol.48 , pp. 377-380
    • Bhuiyan, M.M.H.1
  • 41
    • 2442619128 scopus 로고    scopus 로고
    • Selective reduction of carbon-carbon double bonds of aryl substituted chalcones with Zn=CH3COONH4=C2H5OH=H2O
    • Zhou, J.-B.; Wang, Y.-L.; Wang, J.-Y. Selective reduction of carbon-carbon double bonds of aryl substituted chalcones with Zn=CH3COONH4=C2H5OH=H2O. J. Chem. Res. 2004, 118-119.
    • (2004) J. Chem. Res , pp. 118-119
    • Zhou, J.-B.1    Wang, Y.-L.2    Wang, J.-Y.3
  • 42
    • 37049066004 scopus 로고
    • Chalcones and related compounds, part IX: Preparation and rearrangement of some 1,3-diphenylprop-2-en-1-ols ("chalcols"
    • Davey, W.; Hearne, J. A. Chalcones and related compounds, part IX: Preparation and rearrangement of some 1,3-diphenylprop-2-en-1-ols ("chalcols"). J. Chem. Soc. 1964, 4978-4985.
    • (1964) J. Chem. Soc , pp. 4978-4985
    • Davey, W.1    Hearne, J.A.2
  • 43
    • 0000997887 scopus 로고
    • In situ generation and synthetic application of 2-phenylbenzimidazoline to the selective reduction of carbon-carbon double bonds of electron-deficient olefins
    • Chikashita, H.; Nishida, S.; Miyazaki, M.; Morita, Y.; Itoh, K. In situ generation and synthetic application of 2-phenylbenzimidazoline to the selective reduction of carbon-carbon double bonds of electron-deficient olefins. Bull. Chem. Soc. Japan 1987, 60, 737-746.
    • (1987) Bull. Chem. Soc. Japan , vol.60 , pp. 737-746
    • Chikashita, H.1    Nishida, S.2    Miyazaki, M.3    Morita, Y.4    Itoh, K.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.