The oxidative dehydrogenation of alcohols to aldehydes catalyzed by Ag nanoparticles supported on Al2O3 was studied. The catalyst promoted the direct formation of imines by tandem oxidative dehy-drogenation and condensation of alcohols and amines. The reactions were performed under mild conditions and afforded the imines in high yield (up to 99%) without any byproducts other than H2O. The highest activity was obtained over 5 wt%Ag/Al2O3 in toluene with air as oxidant. The reactions were also performed under oxidant-free conditions where the reaction was driven to the product side by the production of H2 in the gas phase. The use of an efficient and selective Ag cata-lyst for the oxidative dehydrogenation of alcohol in the presence of amines gives a new green reac-tion protocol for imine synthesis.
参考文献
[1] | Franz G;Sheldon R A.‘Oxidation’,Ullmann’s Encyclopedia of In-dustrial Chemistry.6th Ed[M].Weinheim:Wiley-VCH,2000 |
[2] | Mallat T;Baiker A .[J].CHEMICAL REVIEWS,2004,104:3037. |
[3] | Friedrich A;Schneider S .[J].ChemCatChem,2009,1:72. |
[4] | Maggi, A.;Madsen, R. .Dehydrogenative synthesis of imines from alcohols and amines catalyzed by a ruthenium N-heterocyclic carbene complex[J].Organometallics,2012(1):451-455. |
[5] | Rigoli, J.W.;Moyer, S.A.;Pearce, S.D.;Schomaker, J.M. .α,β-Unsaturated imines via Ru-catalyzed coupling of allylic alcohols and amines[J].Organic & biomolecular chemistry,2012(9):1746-1749. |
[6] | Esteruelas, M.A.;Honczek, N.;Oliván, M.;O?ate, E.;Valencia, M. .Direct access to pop-type osmium(II) and osmium(IV) complexes: Osmium a promising alternative to ruthenium for the synthesis of imines from alcohols and amines[J].Organometallics,2011(9):2468-2471. |
[7] | Boopathy G;Jing Z;David M .[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2010,49:1468. |
[8] | Mitsudome T;Mikami Y;Funai H;Mizugaki T.Jitsukawa K,Kaneda K .[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2008,47:138. |
[9] | Shimizu K-i;Sugino K;Sawabe K;Satsuma A .[J].Chemistry-A European Journal,2009,15:2341. |
[10] | Shimizu K-i;Ohshima K;Satsuma A .[J].Chemistry-A European Journal,2009,15:9977. |
[11] | Shimizu K-i;Nishimura M;Satsuma A .[J].ChemCatChem,2009,1:497. |
[12] | Liu H H;Chuah G-K;Jaenicke S .[J].Journal of Catalysis,2012,292:130. |
[13] | Patil R D;Adimurthy S .[J].Asian J Org Chem,2013,2:726. |
[14] | Mielby J;Kegnaes S;Fristrup P .[J].ChemCatChem,2012,4:1037. |
[15] | Kirm I;Medina F;Rodríguez X;Cesteros Y Salagre P Sueiras J .[J].Applied Catalysis A:General,2004,272:175. |
[16] | Li W X;Stampfl C;Scheffler M .[J].Physical Review Letters,2003,90:256102. |
[17] | Yamamoto R;Sawayama Y;Shibahara H;Ichihashi Y;Nishiyama S;Tsuruya S .Promoted partial oxidation activity of supported Ag catalysts in the gas-phase catalytic oxidation of benzyl alcohol[J].Journal of Catalysis,2005(2):308-317. |
[18] | Kegn?s S;Mielby J;Mentzel U V;Christensen C H Riisager A .[J].Green Chemistry,2010,12:1437. |
[19] | Soulé, J.-F.;Miyamura, H.;Kobayashi, S. .Selective imine formation from alcohols and amines catalyzed by polymer incarcerated gold/palladium alloy nanoparticles with molecular oxygen as an oxidant[J].Chemical communications,2013(4):355-357. |
[20] | Grirrane, A.;Corma, A.;Garcia, H. .Highly active and selective gold catalysts for the aerobic oxidative condensation of benzylamines to imines and one-pot, two-step synthesis of secondary benzylamines[J].Journal of Catalysis,2009(2):138-144. |
[21] | Sun H;Su F Z;Ni J;Cao Y He H Y Fan K N .[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2009,48:4390. |
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