A silica supported ionic liquid was synthesized and characterized by scanning electron microscopy (SEM), Fourier transform infrared spectroscopy, X-ray diffraction, N2 adsorption-desorption, and thermogravimetric analysis. All these techniques, especially SEM results indicated the presence of well-defined spherical particles having diameters larger than the pristine silica particles, confirming the successful immobilization of the ionic liquid. The prepared silica supported ionic liquid was used in the reductive amination of cyclohexanone under different conditions with different azeo-tropic mixtures of formic acid and triethyl amine as a hydrogen source. The catalyst showed effi-cient catalytic performance and excellent yields of N-cyclohexyl amine derivatives in the range of 58%to 84%at 30 °C. After completion of the reaction, the catalyst was easily recovered by simple filtration and reused for another five cycles without any significant impact on product yields. The obtained catalytic performance indicates that the present catalyst is green, very active, and reusable for the reductive amination of cyclohexanone.
参考文献
| [1] | Pfruender H;Midjojo M;Kragl U;Weuster-Botz D .[J].Angew Chem Int Edt,2004,43:4529. |
| [2] | Neves C M S S;Freire M G;Coutinho J A P .[J].RSC Adv,2012,2:10882. |
| [3] | DeSimone J M .[J].Science,2002,297:799. |
| [4] | Welton T .[J].Coord Chem Rev,2004,248:2459. |
| [5] | Liu W;Holladay J .[J].Catal Today,2013,200:106. |
| [6] | Anastas P;Eghbali N .[J].Chem Soc Rev,2010,39:301. |
| [7] | Han L;Choi H J;Kim D K;Park S W,Liu B,Park D W .[J].J Mol Catal A,2011,338:58. |
| [8] | Sans V;Gelat F;Karbass N;Burguete M I,Garcia-Verdugo E.Luis S V .[J].Adv Synth Catal,2010,352:3013. |
| [9] | Mehnert CP .Supported ionic liquid phases[J].Chemistry: A European journal,2004(1):50-56. |
| [10] | Werner S;Szesni N;Bittermann A;Schneider M J,Harter P,Hau-mann M,Wasserscheid P .[J].Appl Catal A,2010,377:70. |
| [11] | Ochsner E;Schneider M J;Meyer C;Haumann M,Wasserscheid P .[J].Appl Catal A,2011,399:35. |
| [12] | Li H;Bhadury P S;Song B;Yang S .[J].RSC Adv,2012,2:12525. |
| [13] | Riisager A;Wasserscheid P;van Hal R;Fehrmann R .[J].J Catal,2003,219:452. |
| [14] | Wasserscheid P .[J].J Ind Eng Chem,2007,13:325. |
| [15] | Podolean I;Hardacre C;Goodrich P;Brun N,Backov R,Coman S M,Parvulescu V I .[J].Catal Today,2013,200:63. |
| [16] | Haumann M;Riisager A .[J].Chem Rev,2008,108:1474. |
| [17] | Werner S;Szesni N;Fischer R W;Haumann M,Wasserscheid P .[J].Phys Chem Chem Phys,2009,11:10817. |
| [18] | Gu Y L;Li G X .[J].Adv Synth Catal,2009,351:817. |
| [19] | Mehnert C P .[J].Chem Eur J,2005,11:50. |
| [20] | Tallman,K.R.;Grandy,D.K. .A decade of pharma discovery delivers new tools targeting trace amine-associated receptor 1[J].Neuropsychopharmacology: official publication of the American College of Neuropsychopharmacology,2012(12):2553-2554. |
| [21] | Tarasevich V A;Kozlov N G .[J].Russ Chem Rev,1999,64:55. |
| [22] | Xu Z W;Yan P F;Xu W J;Jia S Y,Xia Z,Chung B,Zhang Z C .[J].RSC Adv,2014,4:59083. |
| [23] | Li C;Villa-Marcos B;Xiao J .[J].J Am Chem Soc,2009,131:6967. |
| [24] | Domine M E;Hernandez-Soto M C;Navarro M T;Perez Y .[J].Catal Today,2011,172:13. |
| [25] | Williams G D;Pike R A;Wade C E;Wills M .[J].Org Lett,2003,5:4227. |
| [26] | Alcock NJ.;Mann I.;Peach P.;Wills M. .Dynamic kinetic resolution-asymmetric transfer hydrogenation of 1-aryl-substituted cyclic ketones[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2002(22):2485-2490. |
| [27] | Gladiali S;Alberico E .Asymmetric transfer hydrogenation: chiral ligands and applications[J].Chemical Society Reviews,2006(3):226-236. |
| [28] | Xie, J.-H.;Zhu, S.-F.;Zhou, Q.-L. .Transition metal-catalyzed enantioselective hydrogenation of enamines and imines[J].Chemical Reviews,2011(3):1713-1760. |
| [29] | Uematsu N;Fujii A;Hashiguchi S;Ikariya T,Noyori R .[J].J Am ChemSoc,1996,118:4916. |
| [30] | Mao J;Baker D C .[J].Org Lett,1999,1:841. |
| [31] | Abdur-Rashid K;Lough A J;Morris R H .[J].Organometallics,2001,20:1047. |
| [32] | Shirai S;Nara H;Kayaki Y;Ikariya T .Remarkable Positive Effect of Silver Salts on Asymmetric Hydrogenation of Acyclic Imines with Cp*Ir Complexes Bearing Chiral N-Sulfonylated Diamine Ligands[J].Organometallics,2009(3):802-809. |
| [33] | Hou, GH;Tao, R;Sun, Y;Zhang, XM;Gosselin, F .Iridium-Monodentate Phosphoramidite-Catalyzed Asymmetric Hydrogenation of Substituted Benzophenone N-H Imines[J].Journal of the American Chemical Society,2010(7):2124-2125. |
| [34] | Surya Prakash G K;Do C;Mathew T;Olah G A .[J].Catal Lett,2010,137:111. |
| [35] | Apodaca R;Xiao W .[J].Org Lett,2001,3:1745. |
| [36] | Drinkel E E;Campedelli R R;Manfredi A M;Fiedler H D,Nome F .[J].J Org Chem,2014,79:2574. |
| [37] | Reddy P S;Kanjilal S;Sunitha S;Prasad R B N .[J].Tetrahedron Lett,2007,48:8807. |
| [38] | Schellenberg K A .[J].J Org Chem,1963,28:3259. |
| [39] | Brown H C;Kanth J V B;Dalvi P V;Zaidlewicz M .[J].J Org Chem,1999,64:6263. |
| [40] | Matsumura T;Nakada M .[J].Tetrahedron Lett,2014,55:1829. |
| [41] | Eschweiler W .[J].Ber Deut Chem Gesell,1905,38:880. |
| [42] | Clarke H T;Gillespie H B;Weisshaus S Z .[J].J Am Chem Soc,1933,55:4571. |
| [43] | Pine S H;Sanchez B L .[J].J Org Chem,1971,36:829. |
| [44] | Imao D;Fujihara S;Yamamoto T;Ohta T;Ito Y .Effective reductive amination of carbonyl compounds with hydrogen catalyzed by iridium complex in organic solvent and in ionic liquid[J].Tetrahedron,2005(29):6988-6992. |
| [45] | Fei Z;Zhao D;Geldbach T J;Scopelliti R,Dyson P J .[J].Chem Eur J,2004,10:4886. |
| [46] | Kolesnikov P N;Yagafarov N Z;Usanov D L;Maleev V I,Chusov D .[J].Org Lett,2015,17:173. |
| [47] | Mirza-Aghayan M;Tavana M M;Rahimifard M;Boukherroub R .[J].Appl Organometal Chem,2014,28:113. |
| [48] | Byun E;Hong B;De Castro K A;Lim M,Rhee H .[J].J Org Chem,2007,72:9815. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分：
-
10%
-
20%
-
30%
-
40%
-
50%