Silica-functionalized N-propylpiperazine for immobilization of palladium nanoparticles as efficient heterogeneous catalyst for cyanation reactions

doi:10.1016/S1872-2067(12)60532-4

Abstract

Abstract:

An efficient heterogeneous Pd catalytic system has been developed, based on immobilization of Pd nanoparticles (PNPs) on a silica-bonded N-propylpiperazine (SBNPP) substrate. The SBNPP substrate effectively stabilizes the PNPs and improves their stability against aggregation. The catalytic activity of this catalyst was investigated in the cyanation of aryl halides with K₄[Fe(CN)₆] as the cyanide source. The catalyst could be recycled several times without appreciable loss of catalytic activity.

Key words: Palladium nanoparticle, Silica-bonded N-propylpiperazine, Cyanation reaction, Aryl halide

Khodabakhsh NIKNAM, Abdollah DERIS, Farhad PANAHI. Silica-functionalized N-propylpiperazine for immobilization of palladium nanoparticles as efficient heterogeneous catalyst for cyanation reactions[J]. Chinese Journal of Catalysis, 2013, 34(4): 718-722.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(12)60532-4

https://www.cjcatal.com/EN/Y2013/V34/I4/718

References

[1] Kleemann A, Engel J, Kutscher B, Reichert D. Pharmaceutical Subtances: Syntheses, Patents, Applications. 4th Ed. Stuttgart: Georg Thieme, 2001

[2] Collier S J, Langer P. Sci Synth, 2004, 19: 403

[3] Rappoport Z. Chemistry of the Cyano Group. 1st Ed. London: John Wiley & Sons, 1970

[4] Chidambaram M, Sonavane S U, De La Zerda J, Sasson Y. Tetrahedron, 2007, 63: 7696

[5] Kitano Y, Manoda T, Miura T, Chiba K, Tada M. Synthesis, 2006, 405

[6] Reddy C R, Madhavi P P, Reddy A S. Tetrahedron Lett, 2007, 48: 7169

[7] Yabe O, Mizufune H, Ikemoto T. Synlett, 2009: 1291

[8] Schareina T, Zapf A, Mägerlein W, Müller N, Beller M. Tetrahedron Lett, 2007, 48: 1087

[9] Schareina T, Jackstell R, Schulz T, Zapf A, Cotte A, Gotta M, Beller M. Adv Synth Catal, 2009, 351: 643

[10] Ren Y L, Dong C H, Zhao S, Sun Y D, Wang J J, Ma J Y, Hou C D. Tetrahedron Lett, 2012, 53: 2825

[11] Chattopadhyay K, Dey R, Ranu B C. Tetrahedron Lett, 2009, 50: 3164

[12] De Blase C, Leadbeater N E. Tetrahedron, 2010, 66: 1098

[13] Zhang J L, Chen X R, Hu T J, Zhang Y, Xu K L, Yu Y P, Huang J. Catal Lett, 2010, 139: 56

[14] Shevlin M. Tetrahedron Lett, 2010, 51: 4833

[15] Hajipour A R, Karami K, Tavakoli G, Pirisedigh A. J Organomet Chem, 2011, 696: 819

[16] Shim Y J, Lee H J, Park S. J Organomet Chem, 2012, 696: 4173

[17] Kianmehr E, Ghanbari M, Faghih N, Rominger F. Tetrahedron Lett, 2012, 53: 1900

[18] Ren Y L, Liu Z F, He S B, Zhao S, Wang J J, Niu R Q, Yin W P. Org Process Res Dev, 2009, 13: 764

[19] Shareina T, Zapf A, Cotte A, Muller N, Beller M. Synthesis, 2008: 3351

[20] Sergeev A G, Schulz T, Torborg C, Spamenberg A, Neumann H, Beller M. Angew Chem, Int Ed, 2009, 48: 7595

[21] Hajipour A R, Karami K, Pirisedigh A. Appl Organometal Chem, 2010, 24: 454

[22] Moussa S, Siamaki A R, Gupton B F, El-Shall M S. ACS Catal, 2012, 2: 145

[23] Cheng J S, Zhang G C, Du J, Tang L H, Xu J Y, Li J H. J Mater Chem, 2011, 21: 3485

[24] Karimi B, Abedi S, Clark J H, Budarin V. Angew Chem, Int Ed, 2006, 45: 4776

[25] Polshettiwar V, Len C, Fihri A. Coord Chem Rev, 2009, 253: 2599

[26] Demel J, Cejka J, Stepnicka P. J Mol Catal A, 2010, 329: 13

[27] Astruc D. Tetrahedron: Asymmetry, 2010, 21: 1041

[28] Firouzabadi H, Iranpoor N, Gholinejad M. J Organomet Chem, 2010, 695: 2093

[29] Corma A, Iborra S, Xamena F X L I, Monton R, Calvino J J, Prestipino C. J Phys Chem C, 2010, 114: 8828

[30] Niknam K, Gharavi A, Hormozi-Nezhad M R, Panahi F, Sharbati M T. Synthesis, 2011: 1609

[31] Khalafi-Nezhad A, Panahi F. Green Chem, 2011, 13: 2408

[32] Richard R. Surface and Nanomolecular Catalysis. London: Taylor & Francis, 2006

[33] Burda C, Chen X, Narayanan R, El-Sayed M A. Chem Rev, 2005, 105: 1025

[34] Niknam K, Deris A, Naeimi F, Majleci F. Tetrahedron Lett, 2011, 52: 4642

[35] Dey R K, Patnaik T, Singh V K, Swain S K, Airoldi C. Appl Surf Sci, 2009, 255: 8176

[36] Horv醫h A, Beck A, S醨k醤y A, Guczi L. Solid State Ionics, 2002, 148: 219

[37] Wang L C, Huang C Y, Chang C Y, Lin W C, Chao K J. Microporous Mesoporous Mater, 2008, 110: 451

[38] van Laren M W, Duin M A, Klerk C, Naglia M, Rogolino D, Pelaratti P, Bacchi A, Pelizzi C, Elsevier C J. Organometallics, 2002, 21: 1546

[39] Kluwer A M, Elsevier C J, Bühl M, Lutz M, Spek A L. Angew Chem, Int Ed, 2003, 42: 3501

[40] van Asselt R, Elsevier C J. Tetrahedron, 1994, 50: 323

[41] Moulder J F, Stickle W F, Sobol P E, Bomben K D. Handbook of X-ray Photoelectron Spectroscopy. USA: Physical Electronics Inc, 1995. 118-119