Recent advances in the heterogeneous palladium-catalysed Suzuki cross-coupling reaction

Current Organic Chemistry

Volumn 16, Issue 9, 2012, Pages 1128-1150

  Mora, Manuel ^a   Jiménez Sanchidrián, César ^a   Ruiz, José Rafael ^a  

^a UNIVERSITY OF CÓRDOBA   (Spain)

Author keywords

Cross coupling reaction; Pd heterogenous catalysts; Suzuki reaction

Indexed keywords

C-C BONDS; CROSS COUPLING REACTIONS; HETEROGENOUS CATALYSTS; INORGANIC SUPPORTS; ORGANICS; PALLADIUM-CATALYZED; PD HETEROGENOUS CATALYST; SUZUKI CROSS COUPLING REACTIONS; SUZUKI REACTION; ]+ CATALYST;

CATALYSIS;

EID: 84862523198     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527212800564358     Document Type: Review

References (146)

1. Miyaura, N.; Suzuki, A. The palladium-catalyzed head-to-tail crosscoupling reaction of 1-alkenylboranes with phenyl or 1-alkenyl iodides. A novel synthesis of 2-phenyl-1-alkenes or 2-alkyl-1,3-alkadienes via organoboranes. J. Organomet. Chem. 1981, 212, C53-C56.
2. Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457-2483.
3. Chemler, S. R.; Trauner, D.; Danishefsky, J. The B-alkyl Suzuki-Miyaura cross-coupling reaction: a versatile C-C bond-forming tool. Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
4. Kotha, S.; Lahiri, K.; Kashinath, D. Recent applications of the Suzuki- Miyaura cross-coupling reaction in organic synthesis. Tetrahedron 2002, 58, 9633.
5. Bellina, F.; Carpita, A.; Rossi, R. Palladium catalysts for the Suzuki crosscoupling reaction: An overview of recent advances. Synthesis 2004, 15, 2419.
6. Nishiyama, N.; Yamamoto, T.; Koie, Y. Synthesis of N-arylpiperazines from aryl halides and piperazine under a palladium tri-tert-butylphosphine catalyst. Tetrahedron Lett. 1998, 39, 617-620.
7. Hartwig, J. F.; Richards, S.; Baranano, D.; Paul, F. Influences on the relative rates for C-N bond-forming reductive elimination and β-hydrogen elimination of amides. A case study on the origins of competing reduction in the palladium- catalyzed amination of aryl halides. J. Am. Chem. Soc. 1996, 118, 36263633.
8. Paul, F.; Patt, J.; Hartwing, J. F. Structural characterization and simple synthesis of {Pd[P(o-Tol)3]2}, dimeric palladium(II) complexes obtained by oxidative addition of aryl bromides, and corresponding monometallic amine complexes. Organometallics, 1995, 14, 3030-3039.
9. Louie, J.; Hartwig, J. F. Transmetalation involving organotin aryl, thiolate, and amide compounds. An unusual type of dissociative ligand substitution reaction. J. Am. Chem. Soc. 1995, 117, 11598-11599.
10. Littke, A. F.; Fu, G. C. 9 A convenient and general method for Pd-catalyzed Suzuki cross-couplings of aryl chlorides and arylboronic acids. Angew. Chem. Int. Ed. 1999, 37, 3387-3388.
11. Littke, A. F.; Dai, C. Y.; Fu, G. C. Versatile catalysts for the Suzuki crosscoupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions. J. Am. Chem. Soc. 2000, 122, 4020-4028.
12. Lamblin, M.; Nassar-Hardy, L.; Hierso, J.-C.; Fouquet, E.; Felpin, F.-X. Recyclable heterogeneous palladium catalysts in pure water: sustainable developments in Suzuki, Heck, Sonogashira and Tsuji-Trost reactions. Adv. Synth. Catal. 2010, 352, 33-79.
13. Phan, N. T. S.; Van der Sluys, M.; Jones, C. W. On the nature of the active species in palladium catalyzed Mizoroki-Heck and Suzuki-Miyaura couplings - Homogeneous or heterogeneous catalysis, a critical review. Adv. Synth. Catal. 2006, 348, 609-679.
14. Narayanan, R. Recent advances in noble metal nanocatalysts for Suzuki and Heck cross-coupling reactions. Molecules 2010, 15, 2124-2138.
15. Alonso, F.; Beletskaya, I. P.; Yus, M. Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical review. Part 2: the Suzuki reaction. Tetrahedron, 2008, 64, 3047-3101.
16. Corma, A.; Garcia, H. Silica-bound homogenous catalysts as recoverable and reusable catalysts in organic synthesis. Adv. Synth. Catal. 2006, 348, 1391-1412.
17. Mubofu, E. B.; Clark, J. H.; Macquarrie, D. J. A novel Suzuki reaction system based on a supported palladium catalyst. Green Chem. 2003, 3, 23-25.
18. Bedford, R. B.; Cazin, S. J.; Hursthouse, M. B.; Light, M. E.; Pike, K. J.; Wimperis, S. Silica-supported imine palladacycles-recyclable catalysts for the Suzuki reaction? J. Organomet. Chem. 2001, 633, 173-181.
19. Baleizao, C.; Corma, A.; García, H.; Leyva, A. Oxime carbapalladacycle covalently anchored to high surface area inorganic supports or polymers as heterogeneous green catalysts for the Suzuki reaction in water. J. Org. Chem. 2004, 69, 439-446.
20. Albisson, D. A.; Bedford, R. B.; Scully, P. N. Orthopalladated triarylphosphite complexes as highly efficient catalysts in the Heck reaction. Tetrahedron Lett. 1998, 39, 9793-9796.
21. Bedford, R. B.; Cazin, C. S. J.; Holden, D. The development of palladium catalysts for C-C and C-heteroatom bond forming reactions of aryl chloride substrates. Coord. Chem. Rev. 2004, 248, 2283-2321.
22. Bedford, R. B.; Blake, M. E.; Butts, C. P.; Holder, D. The Suzuki coupling of aryl chlorides in TBAB-water mixtures. Chem. Commum. 2003, 466-467.
23. Reetz, M. T.; De Vries, J. G. Ligand-free Heck reactions using low Pdloading. Chem. Commun. 2004, 1559-1553.
24. Botella, L.; Nájera, C. A convenient oxime-carbapalladacycle-catalyzed suzuki cross-coupling of aryl chlorides in water. Angew. Chem. Int. Ed. 2002, 41, 179-181.
25. Alonso, D. A.; Nájera, C.; Pacheco, M. C. Oxime-derived palladium complexes as very efficient catalysts for the Heck-Mizoroki reaction. Adv. Synth. Catal. 2002, 344, 172-183.
26. Alonso, D. A.; Nájera, C.; Pacheco, M. C. Highly active oxime-derived palladacycle complexes for Suzuki-Miyaura and Ullmann-type coupling reactions. J. Org. Chem. 2002, 67, 5588-5594.
27. Corma, A.; Das, D.; García, H.; Leyva, A. A periodic mesoporous organosilica containing a carbapalladacycle complex as heterogeneous catalyst for Suzuki cross-coupling. J. Catal. 2005, 229, 322-331
28. Herrmann, W. A.; Reisinger, C. P.; Splieger, M. Chelating N-heterocyclic carbene ligands in palladium-catalyzed heck-type reactions. J. Organomet. Chem. 1998, 557, 93-96.
29. Weskamp, T.; Böhm, V. P. M.; Herrmann, W. A. Combining N-heterocyclic carbenes and phosphines: Improved palladium(II) catalysts for aryl coupling reactions. J. Organomet. Chem. 1999, 585, 348-352.
30. Tyrrell, E.; Whiteman, L.; Williams, N. The synthesis and characterisation of immobilised palladium carbene complexes and their application to heterogeneous catalysis. J. Organomet. Chem. 2011, 696, 3465-3472.
31. Qiu, H.; Sarkar, S. M.; Lee, D. H.; Jin, M. J. Highly effective silica gelsupported N-heterocyclic carbene-Pd catalyst for Suzuki-Miyaura coupling reaction. Green Chem. 2008, 10, 37-40.
32. Karimi, B.; Enders, D. New N-heterocyclic carbene palladium complex/ionic liquid matrix immobilized on silica: Application as recoverable catalyst for the Heck reaction. Org. Lett. 2006, 8, 1237-1240.
33. Jokic, N.; Straubinger, C. S.; Goh, S. L. M.; Herdtweck, E.; Herrmann, W. A; Kühn, F. E. Symmetrical bis-(NHC) palladium(II) complexes: Synthesis, structure, and application in catalysis. Inorg. Chim. Acta 2010, 363, 4181-4188.
34. Tandukar, S.; Sen, Y. N-heterocyclic carbene-palladium complex immobilized on silica nanoparticles. Recyclable catalyst for high yield Suzuki and Heck coupling reactions under mild conditions. J. Mol. Catal. A: Chemical 2007, 268, 112-119.
35. Paul, S.; Clark, J. H. Structure-activity relationship between some novel silica supported palladium catalysts: A study of the Suzuki reaction. J. Mol. Catal. A: Chemical 2004, 215, 107-111.
36. Leyva, A.; García H.; Corma, A. A soluble polyethyleneglycol-anchored phosphine as a highly active, reusable ligand for Pd-catalyzed couplings of aryl chlorides: comparison with cross and non-cross-linked polystyrene and silica supports. Tetrahedron 2007, 63, 7097-7111.
37. Paetzold, E.; Oehme, G.; Fuhrmann, H.; Richter, M.; Eckelt, R.; Pohl, M. M.; Kosslic, H. Comparison of mesaporous silica and alumina supports for palladium-catalyzed carbon-carbon coupling reactions: Unexpected high acceleration by supported cetyltrimethylammonium bromide. Microp. Mesop. Mat. 2001, 44-45, 517-522.
38. Kosslick, H.; Mönnich, I.; Paetzold, E.; Fuhrmann, H.; Fricke, R.; Müller, D.; Oehme, G. Suzuki reaction over palladium-complex loaded MCM-41 catalysts. Microp. Mesop. Mat. 2001, 44-45, 537-545.
39. Gurbuz, N.; Ozdemir, I.; Cetinkaya, B.; Secklin, T. Silica-supported 3-4,5- dihydroimidazol-1-yl-propyltriethoxysilanedichloropalladium(II) complex: Heck and Suzuki cross-coupling reactions. Appl. Organomet. Chem. 2003, 17, 776-780.
40. Shimizu, K.; Koizumi, S.; Hatamachi, T.; Yoshida, H.; Komai, S.; Kodama, T.; Kitayama, Y. Structural investigations of functionalized mesoporous silica- supported palladium catalyst for Heck and Suzuki coupling reactions. J. Catal. 2004, 228, 141-151.
41. Blanco, B.; Mehdi, A.; Moreno-Mañas, M.; Pelixats, R.; Reyé, C. A macrocyclic triolefinic palladium(0) complex covalently anchored to a mesostructured silica as active and reusable catalyst for Suzuki cross-coupling reactions. Tetrahedron Lett. 2004, 45, 8789-8791.
42. Trilla, M.; Pleixats, R.; Man, M. W. C.; Bied, C.; Moreau, J. J. E. Hybrid organic-inorganic silica materials containing di(2-pyridyl)methylaminepalladium dichloride complex as recyclable catalysts for Suzuki crosscoupling reactions. Tetrahedron Lett. 2006, 47, 2399-2403.
43. Tzschucke, C. C.; Andrushko, V.; Bannwarth, W. Assessment of the reusability of Pd complexes supported on fluorous silica gel as catalysts for Suzuki couplings. Eur. J. Org. Chem. 2005, 5248-5261.
44. Al-Hashimi, M.; Sullivan, A. C.; Wilson, J. R. H. Palladium ethylthioglycolate modified silica-a new heterogeneous catalyst for Suzuki and Heck crosscoupling reactions. J. Mol. Catal. A: Chemical 2007, 273, 298-302.
45. Cai, M.; Xu, Q.; Huang, Y. Heterogeneous Suzuki reaction catalyzed by MCM-41-supported sulfur palladium(0) complex. J. Mol. Catal. A: Chemical 2007, 271, 93-97.
46. Bhunia, S.; Sen, R.; Koner, S. Anchoring of palladium(II) in chemically modified mesoporous silica: An efficient heterogeneous catalyst for Suzuki cross-coupling reaction. Inorg. Chim. Acta 2010, 363, 3993-3999.
47. El-Hankari, S.; El-Kadib, A.; Finiels, A.; Bouhaouss, A.; Moreau, J. J. E.; Crudden, C. M.; Brunel, D.; Hesemann, P. SBA-15-type organosilica with 4- mercapto-N,N-bis-(3-Si-propyl)butanamide for palladium scavenging and cross-coupling catalysis. Chem. Eur. J. 2011, 17, 8984-8994.
48. Islam, S. M.; Mondal, P.; Tuhina, K.; Roy, A. S.; Mondal, S.; Hossain, D. Highly efficient recyclable heterogeneous palladium catalyst for C-C coupling, amination and cyanation reactions. J. Organomet. Chem. 2010, 695, 2284-2295.
49. Islam, S. M.; Mondal, P.; Tuhina, K.; Roy, A. S.; Mondal, S.; Hossain, D. A reusable polymer-anchored palladium(II) schiff base complex catalyst for the suzuki cross-coupling, heck and cyanation reactions. J. Inorg. Organomet. Polym. Mater. 2010, 20, 264-267.
50. Islam, S. M.; Mondal, P.; Roy, A. S.; Mondal, S.; Hossain, D. Heterogeneous Suzuki and copper-free Sonogashira cross-coupling reactions catalyzed by a reusable palladium(II) complex in water medium. Tetrahedron Lett. 2010, 51, 2067-2070.
51. Kim, J.-H.; Kim, J.-W.; Shokouhimehr, M.; Lee, Y.-S. Polymer-supported N-heterocyclic carbine-palladium complex for heterogeneous Suzuki crosscoupling reaction. J. Org. Chem. 2005, 70, 6714-6720.
52. He, Y.; Wang, L.; Cai, C. Diethanol amine-functionalized polymer-supported palladium (0) complex as catalyst for Suzuki cross-coupling reaction in water. J. Appl. Polymer Sci. 2011, 121, 286-291.
53. He, Y.; Cai, C. Polymer-supported macrocyclic Schiff base palladium complex: An efficient and reusable catalyst for Suzuki cross-coupling reaction under ambient condition. Catal. Commun. 2011, 12, 678-683.
54. Suzuka, T.; Nagamine, T.; Ogihara, K.; Higa, M. Suzuki-miyaura crosscoupling reaction in water with polymer-supported terpyridine palladium complex under aerobic conditions. Catal. Lett. 2010, 139, 85-89.
55. Gil-Moltó, J.; Karlstrom, S.; Nájera, C. Di(2-pyridyl)methylamine-palladium dichloride complex covalently anchored to a styrene-maleic anhydride copolymer as recoverable catalyst for C-C cross-coupling reactions in water. Tetrahedron. 2005, 61, 12168-12176.
56. Phan, N. T. S.; Brown, D. H.; Styring, P. A polymer-supported salen-type palladium complex as a catalyst for the Suzuki-Miyaura cross-coupling reaction. Tetrahedron Lett. 2004, 45, 7915-7919.
57. Phan, N. T. S.; Styring, P. Supported phosphine-free palladium catalysts for the Suzuki-Miyaura reaction in aqueous media. Green Chem. 2008, 10, 1055-1060.
58. He, Y.; Cai, C. Tetrazole functionalized polymer supported palladium complex: An efficient and reusable catalyst for the room-temperature Suzuki cross-coupling reaction. Catal. Lett. 2010, 140, 153-159.
59. Bai, L.; Zhang, Y.; Wang, J. X. Rapid microwave-promoted cross-coupling reaction of aryl bromides with aryl boronic acids and sodium tetraphenylborate catalyzed by a reusable polymer-supported palladium complex. QSAR Comb. Sci. 2004, 23, 875-882.
60. Bai, L.; Wang, J. X. Reusable, polymer-supported, palladium-catalyzed, atom-efficient coupling reaction of aryl halides with sodium tetraphenylborate in water by focused microwave irradiation. Adv. Synth. Catal. 2008, 350, 315-320.
61. Varma, R. S.; Naicker, K. P. Synthesis of allylbenzenes: By cross-coupling of allyl bromide with arylboronic acids using a palladium chloride and tetraphenylphosphonium bromide intercalated clay catalyst. Green Chem. 1999, 1, 247-249.
62. Varma, R. S.; Naicker, K. P. Palladium chloride/tetraphenylphosphonium bromide intercalated clay: New catalyst for cross-coupling of aryl halides with arylboronic acids. Tetrahedron Lett. 1999, 40, 439-442.
63. Ruiz, J. R.; Jiménez-Sanchidrián, C.; Mora, M. Suzuki cross-coupling reaction of fluorobenzene with heterogeneous palladium catalysts. J. Fluor. Chem. 2006, 127, 443-445.
64. Jiménez-Sanchidrián, C.; Mora, M.; Ruiz J. R. Suzuki cross-coupling reaction over a palladium-pyridine complex immobilized on hydrotalcite Catal. Commun. 2006, 7, 1025-1028.
65. Mora, M.; Jiménez-Sanchidrián, C.; Ruiz, J. R. Heterogeneous Suzuki crosscoupling reactions over palladium/hydrotalcite catalysts. J. Coll. Interf. Sci. 2006, 302, 568-575.
66. Mora, M.; Jiménez-Sanchidrián, C.; Ruiz, J. R. Suzuki cross-coupling reaction of aryl and heterocyclic bromides and aromatic polybromides on a Pd(II)-hydrotalcite catalyst. Appl. Organomet. Chem. 2008, 21, 122-127.
67. Ruiz, J. R.; Jiménez-Sanchidrián, C.; Mora, M. Palladium supported on hydrotalcite as a catalyst for the Suzuki cross-coupling reaction. Tetrahedron 2006, 62, 2922-2926.
68. Liu, B.; Liu, Z.; Liu, M.; Pan, C.; Ding, J.; Wu, H.; Cheng, J. Aminophosphine supported on Al2O3 as recoverable catalyst for the Suzuki coupling. Catal. Commun. 2007, 8, 2150-2152.
69. Mark, G.; Villiger, A.; Buchecker, R. Aryl couplings with heterogeneous palladium catalysts. Tetrahedron Lett. 1994, 35, 3277-3280.
70. LeBlond, C. R.; Andrews, A.; Sun, Y.; Sowa, J. R. Activation of aryl chlorides for Suzuki cross-coupling by ligandless, Heterogeneous Palladium. Org. Lett. 2001, 3, 1555-1557.
71. Tagata, T.; Nishida, M. Palladium charcoal-catalyzed Suzuki-Miyaura coupling to obtain arylpyridines and arylquinolines J. Org. Chem. 2003, 68, 9412-9415.
72. Simeone, J. P.; Sowa, J. R. Palladium on carbon as a precatalyst for the Suzuki-Miyuara cross-coupling of aryl chlorides. Tetrahedron 2007, 63, 12646-12654.
73. Arcadi, A.; Crichelli, G.; Chiarini, M.; Correa, M.; Zorzan, D. A mild and versatile method for palladium-catalyzed cross-coupling of aryl halides in water and surfactants. Eur. J. Org. Chem. 2003, 4080-4086.
74. Arvela, R.K; Leadbeater, N. E. Suzuki coupling of aryl chlorides with phenylboronic acid in water, using microwave heating with simultaneous cooling. Org. Lett. 2005, 7, 2101-2104.
75. Lysen, M.; Köhler, K. Suzuki-Miyaura cross-coupling of aryl chlorides in water using ligandless palladium on activated carbon. Synlett. 2005, 1671-1674.
76. Lysen, M.; Köhler, K. Palladium on activated carbon - A recyclable catalyst for Suzuki-Miyaura cross-coupling of aryl chlorides in water. Synthesis 2006, 692-689.
77. Soomro, S. S.; Röhlich, C.; Köhler, K. Suzuki coupling reactions in pure water catalyzed by supported palladium -relevance of the surface polarity of the support. Adv. Synth. Catal. 2011, 353, 767-775.
78. Maegawa, T.; Kitamura, Y.; Sako S.; Sakurai, A.; Tanaka, A.; Kobayashi, Y.; Endo, K.; Bora, U.; Kurita, T.; Kozaki, A.; Monguchi, Y.; Sajiki, H. Heterogeneous Pd/C-catalyzed ligand-free, room-temperature suzuki-miyaura coupling reactions in aqueous media. Chem. Eur. J. 2007, 13, 5937-5943.
79. Chen, J. S.; Vasiliev, A. N.; Panarello, A. P.; Khinast, J. G. Pd-leaching and Pd-removal in Pd/C-catalyzed Suzuki couplings. Appl. Catal. A: General 2007, 325, 7686.
80. Conlon, D. A.; Pipik, B.; Ferdinand, S.; Leblond, C. R.; Sowa, J. R.; Izzo, B.; Collins, P.; Ho, G. J.; Williams, J. M.; Shi, Y. J.; Sun, Y. K. Suzuki-Miyaura Cross-Coupling with Quasi-Heterogeneous Palladium. Adv. Synth. Catal. 2003, 345, 931-935.
81. Kitamura, Y.; Sako, S.; Tsutsui, A.; Monguchi, Y.; Maegawa, T.; Kitade, Y.; Sajiki, H. Ligan-free and heterogeneous palladium on carbon-catalyzed hetero- Suzuki-Miyaura cross-coupling. Adv. Synth. Catal. 2010, 352, 718-730.
82. Bykov, V. V.; Bumagin, N. A. Effect of water on the palladium-catalyzed reaction of styrene with iodobenzene. Russ. Chem. Bull. 1997, 46, 1344-1349.
83. Lu, G.; Franzen, R.; Zhang, Q.; Xu, Y. Palladium charcoal-catalyzed, ligandless Suzuki reaction by using tetraarylborates in water. Tetrahedron Lett. 2005, 46, 4255-4259.
84. Organ, M. G.; Mayer, S. Synthesis of 4-(5-iodo-3-methylpyrazolyl) phenylsulfonamide and its elaboration to a COX II inhibitor library by solutionphase Suzuki coupling using Pd/C as a solid-supported catalyst. J. Comb. Chem. 2003, 5, 118-124.
85. Sakurai, H.; Tsukuda, T.; Hirao, T. Pd/C as a reusable catalyst for the coupling reaction of halophenols and arylboronic acids in aqueous media. J. Org. Chem. 2002, 67, 2721-2722.
86. Khedkar, M. V.; Tambade, P. J.; Qureshi, Z. S.; Blanage, B. M. Pd/C: An efficient, heterogeneous and reusable catalyst for phosphane-free carbonylative suzuki coupling reactions of aryl and heteroaryl iodides Eur. J. Org. Chem. 2010, 6981-6986.
87. Corma, A.; García, H.; Leyva, A. Bifunctional palladium-basic zeolites as catalyst for Suzuki reaction. Appl. Catal. A: General 2002, 236, 179-185.
88. Bulut, H.; Artok, L.; Yilmaz, S. Suzuki cross-coupling reaction of aryl halides with arylboronic acids catalysed by Pd(II)-NaY zeolite. Tetrahedron Lett. 2003, 44, 289-291.
89. Durgun, G.; Aksin, O.; Artok, L. Pd-loaded NaY zeolite as a highly active catalyst for ligandless Suzuki-Miyaura reactions of aryl halides at low Pd loadings under aerobic conditions. J. Mol. Catal. A: Chemical 2007, 278, 189-199.
90. Okumura, K.; Tomiyama, T.; Okuda, S.; Yoshida, H.; Kiwa, M. Origin of the excellent catalytic activity of Pd loaded on ultra-stable y zeolites in Suzuki- Miyaura reactions. J. Catal. 2010, 273, 156-166.
91. Leadbeater, N. E. Fast, easy, clean chemistry by using water as a solvent and microwave heating: The Suzuki coupling as an illustration. Chem. Commun. 2005, 2881-2902.
92. Reetz, M. T.; de Vries, J. G. Ligand-free Heck reactions using low Pdloading. Chem. Commun. 2004, 1559-1563.
93. Artok, L.; Bulut, H. Heterogeneous Suzuki reactions catalyzed by Pd(0)-Y zeolite. Tetrahedron Lett. 2004, 45, 3881-3884.
94. Durap, F.; Rakap, M.; Aydemir, M.; Özkar, S. Room temperature aerobic Suzuki cross-coupling reactions in DMF/water mixture using zeolite confined palladium(0) nanoclusters as efficient and recyclable catalyst. Appl. Catal. A: General 2010, 382, 339-344.
95. Choi, M.; Lee, D.-H.; Na, K.; Yu, B.-W., Ryoo, R. High catalytic activity of palladium (II)-exchanged mesoporous sodalite and NaA zeolite for bulky aryl coupling reactions: reusability under aerobic conditions. Angew. Chem. Int. Ed. 2009, 48, 3673-3676.
96. Mora, M.; López, M. I.; Carmona, M. A.; Jiménez-Sanchidrián, C.; Ruiz, J. R. Study of the thermal decomposition of a sepiolite by mid- and nearinfrared spectroscopies. Polyhedron 2010, 29, 3046-3051.
97. Kitayama, Y.; Shimizu, K.; Kodama, T.; Murai, S.; Mizusima, T.; Hayakawa, M.; Muruoka, M. Role of intracrystalline tunnels of sepiolite for catalytic activity. Stud. Surf. Sci. Catal. 2002, 142, 675-682.
98. Shimizu, K.; Kan-no, T.; Kodama, T.; Hagiwara, H.; Kitayama, Y. Suzuki cross-coupling reaction catalyzed by palladium-supported sepiolite. Tetrahedron Lett. 2002, 43, 5653-5655.
99. Shimizu, K.; Maruyama, R.; Komai, S.; Kodama, T.; Kitayama, Y. Pdsepiolite catalyst for Suzuki coupling reaction in water: Structural and catalytic investigations. J. Catal. 2004, 227, 202-209.
100. Corma, A.; García, H.; Leyva, A.; Primo, A. Alkali-exchanged sepiolites containing palladium as bifunctional (basic sites and noble metal) catalysts for the Heck and Suzuki reactions. Appl. Catal. A: General 2004, 257, 77-83.
101. Corma, A.; García, H.; Primo, A.; Domenech, A. A test reaction to assess the presence of Brönsted and the softness/hardness of Lewis acid sites in palladium supported catalysts. New J. Chem. 2004, 28, 361-365.
102. Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. Layered double hydroxide supported nanopalladium catalyst for Heck-, Suzuki-, Sonogashira-, and Stille-type coupling reactions of chloroarenes. J. Am. Chem. Soc. 2002, 124, 14127-14136.
103. Das, D. D.; Sayari, A. Applications of pore-expanded mesoporous silica 6. Novel synthesis of monodispersed supported palladium nanoparticles and their catalytic activity for Suzuki reaction. J. Catal. 2007, 246, 60-65.
104. Jana, S.; Haldar, S.; Koner, S. Heterogeneous Suzuki and Stille coupling reactions using highly efficient palladium(0) immobilized MCM-41 catalyst. Tetrahedron Lett. 2009, 50, 4820-4823.
105. Han, P.; Wang, X.; Qiu, X.; Ji, X.; Gao, L. One-step synthesis of palladium/ SBA-15 nanocomposites and its catalytic application. J. Mol. Catal. A: Chemical 2007, 272, 136-141.
106. Zheng, Z.; Li, H.; Liu, T.; Cao, R. Monodisperse noble metal nanoparticles stabilized in SBA-15: Synthesis, characterization and application in microwave- assisted Suzuki-Miyaura coupling reaction. J. Catal. 2010, 270, 268-274.
107. Budroni, G.; Corma, A.; García, H.; Primo, A. Pd nanoparticles embedded in sponge-like porous silica as a Suzuki-Miyaura catalyst: Similarities and differences with homogeneous catalysts J. Catal. 2007, 251, 345-353.
108. Davis, J. N.; Matty, D. L.; Hughes, D. J.; Reider, P. J. Are heterogeneous catalysts precursors to homogeneous catalysts? J. Am. Chem. Soc. 2001, 123, 10139-10140.
109. Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. One-pot synthesis of recyclable palladium catalysts for hydrogenations and carbon-carbon coupling reactions. Tetrahedron Lett. 2004, 45, 7057-7059.
110. Bedford, R. B.; Sing, U. G.; Walton, R. I.; Williams, R. T.; Davis, S. A. Nanoparticulate palladium supported by covalently modified silicas: Synthesis, characterization, and application as catalysts for the Suzuki coupling of aryl halides. Chem. Mater. 2005, 17, 701-707.
111. Crudden, C. M.; Sateesh, M.; Lewis, R. Mercaptopropyl-modified mesoporous silica: A remarkable support for the preparation of a reusable, heterogeneous palladium catalyst for coupling reactions. J. Am. Chem. Soc. 2005, 127, 10045-10050.
112. Shin, J. Y.; Lee, B. S.; Jung, Y.; Kim, S. J.; Lee, S. Palladium nanoparticles captured onto spherical silica particles using a urea cross-linked imidazolium molecular band. Chem. Commun. 2007, 5238-5240.
113. Dutta, P.; Sarkar, A. Palladium nanoparticles immobilized on chemically modified silica gel: efficient heterogeneous catalyst for Suzuki, Stille and Sonogashira cross-coupling reactions. Adv. Synth. Catal. 2011, 353, 2814-2822.
114. Kudo, D.; Masui, Y.; Onaka, M. An efficient heterogeneous Pd catalyst for the Suzuki coupling: Pd/Al2O3 Chem. Lett. 2007, 36, 918-919.
115. Köhler, K.; Heidenreich, R. G.; Soomro, S. S.; Pröckl, S. S. Supported palladium catalysts for suzuki reactions: Structure-property relationships, optimized reaction protocol and control of palladium leaching. Adv. Synth. Catal. 2008, 350, 2930-2936.
116. Soomro, S. S.; Ansari, F. L.; Chatziapostolou, K.; Köhler, K. Palladium leaching dependent on reaction parameters in Suzuki-Miyaura coupling reactions catalyzed by palladium supported on alumina under mild reaction conditions. J. Catal. 2010, 273, 138-146.
117. Gniewek, A.; Ziolkowski, J. J.; Trzeciak, A. M.; Zawadzki, M.; Grabowska, H.; Wrzystzcs, J. Palladium nanoparticles supported on alumina-based oxides as heterogeneous catalysts of the Suzuki-Miyaura reaction J. Catal. 2008, 254, 121-130.
118. Hagiwara, H.; Keon, K. H.; Hashi, T. Supported ionic liquid catalyst (Pd- SILC) for highly efficient and recyclable Suzuki-Miyaura reaction Chem. Commun. 2007, 2838-2840.
119. Hagiwara, H.; Keon, K. H.; Hashi, T. Sustainable Suzuki-Miyaura reaction catalyzed by Pd(OAc)2 immobilized on reversed-phase alumina. Synlett. 2008, 611-613.
120. Okubo, K.; Shirai, M.; Yokoyama, C. Heck reactions in a non-aqueous ionic liquid using silica supported palladium complex catalysts. Tetrahedron Lett. 2002, 43, 7115-7118.
121. Kabalka, G. W.; Pagni, R. M.; Hair, C. M. Solventless Suzuki coupling reactions on palladium-doped KF/Al2O3. Org. Lett. 1999, 1, 1423-1425.
122. Bernhardt, F.; Trotzki, R.; Szuppa, T.; Stolle, A.; Ondruschka, B. Solventfree and time-efficient Suzuki-Miyaura reaction in a ball mill: The solid reagent system KF-Al2O3 under inspection. Beil. J. Org. Chem. 2010, 6, 1-7.
123. Basu, B.; Das, P.; M. M. H. Bhuiyan, Jha, S. Microwave-assisted Suzuki coupling on a KF-alumina surface: Synthesis of polyaryls. Tetrahedron Lett. 2003, 44, 3817-3820.
124. Kogan, V.; Aizenshtat, Z.; Popovitz-Biro, R.; Neuman, R. Carbon-carbon and carbon-nitrogen coupling reactions catalyzed by palladium nanoparticles derived from a palladium substituted Keggin-type polyoxometalate. Org. Lett. 2002, 4, 3529-3532.
125. Paira, R.; Sahu, K. B.; Mondal, S.; Maity, A.; Hazras, A.; Naskar, S.; Saha, P.; Padmanaban, E.; Banerjee, S.; Mondal, N. B. Effective Suzuki-Miyaura arylation and sonogashira aryl alkynylation on N-heteroaromatic cations: Synthesis of substituted pyridine-fused cationic heterocycles. Synthesis 2011, 3006-3014.
126. Kantam, M. L.; Roy, S.; Roy, M.; Sreedhar, B.; Choudary, B. M. Nanocrystalline magnesium oxide-stabilized palladium(0): An efficient and reusable catalyst for Suzuki and stille cross-coupling of aryl halides. Adv. Synth. Catal. 2005, 347, 2002-2008.
127. Cwik, A.; Hell, Z.; Figureras, F. Suzuki-Miyaura cross-coupling reaction catalyzed by Pd/MgLa mixed oxide. Org. Biomed. Chem. 2005, 3, 4307-4309.
128. Andrews, S. P.; Stepan, A. F.; Tanaka, H.; Ley, S. U.; Smith, M. D. Heterogeneous or homogeneous? A case study involving palladium-containing perovskites in the Suzuki reaction. Adv. Synth. Catal. 2005, 347, 647-654.
129. Kantam, M. L.; Kumar, K. B. S.; Srinivas, P.; Sreedhar, B. Fluorapatitesupported palladium catalyst for Suzuki and Heck coupling reactions of haloarenes. Adv. Synth. Catal. 2007, 349, 1141-1149.
130. Sreedhar, B.; Yada, D.; Reddy, P. S. Nanocrystalline titania-supported palladium (0) nanoparticles for Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides. Adv. Synth. Catal. 2011, 353, 2823-2836.
131. Strimbu, L.; Liu, J.; Kaifer, A. E. Cyclodextrin-capped palladium nanoparticles as catalysts for the Suzuki reaction. Langmuir 2003, 19, 483-485.
132. Liu, J.; Álvarez, J.; Ong, W.; Román, E.; Kaifer, A. E. Tuning the catalytic activity of cyclodextrin-modified palladium nanoparticles through host-guest binding interactions. Langmuir 2001, 17, 6762-6764.
133. Senra, J. D.; Malta, L. F. B.; da Costa, M. E. H. M.; Michel, R. C.; Aguiar, L. C. S.; Simas, A. B. C.; Antunes, O. A. C. Hydroxypropyl-a-cyclodextrincapped palladium nanoparticles: active scaffolds for efficient carbon-carbon bond forming cross-couplings in water. Adv. Synth. Catal. 2009, 351, 2411-2422.
134. Islam R. U.; Witcomb, M. J.; var der Lingen, E.; Scurrel, M. S.; van Otterio, W. V.; Mallick, K. In-situ synthesis of a palladium-polyaniline hybrid catalyst for a Suzuki coupling reaction. J. Organomet. Chem. 2011, 696, 2206-2210.
135. Kantam, M. L.; Roy, M.; Roy, S.; Sreedhar, B.; Madhavendra, S. S.; Choudary, B. M.; De R. L. Polyaniline supported palladium catalyzed Suzuki- Miyaura cross-coupling of bromo- and chloroarenes in water Tetrahedron 2007, 63, 8002-8009.
136. Houdayer, A.; Schneider, R.; Billaud, D.; Ghanbaja, J.; Lambert, J. Heck and Suzuki-Miyaura couplings catalyzed by nanosized palladium in polyaniline. Appl. Organomet. Chem. 2005, 19, 1239-1248.
137. Gallon, B. J.; Kojima, R. W.; Kaner, R. B.; Diaconescu, P. L. Palladium nanoparticles supported on polyaniline nanofibers as a semi-heterogeneous catalyst in water. Angew. Chem. Int. Ed. 2007, 46, 7251-7254.
138. Lemo, J.; Heuzé, K.; Astruc, D. Synthesis and catalytic activity of DABdendrimer encapsulated Pd nanoparticles for the Suzuki coupling reaction. Inorg. Chim. Acta 2006, 359, 4909-4911.
139. Astruc, D. Palladium catalysis using dendrimers: Molecular catalysts versus nanoparticles. Tetrahedron: Asym. 2010, 21, 1041-1054.
140. Piao, Y.; Juang, Y.; Shokouhimehr, M.; Lee, I. S.; Hyeon, T. Facile aqueousphase synthesis of uniform palladium nanoparticles of various shapes and sizes Small 2007, 3, 255-260.
141. Wang, J.; Song, G.; Peng, Y. Reusable Pd nanoparticles immobilized on functional ionic liquid co-polymerized with styrene for Suzuki reactions in water-ethanol solution. Tetrahedron Lett. 2011, 52, 1477-1480.
142. Metin, O.; Durap, F.; Aydemir, M.; Özkar, S. Palladium(0) nanoclusters stabilized by poly(4-styrenesulfonic acid-co-maleic acid) as an effective catalyst for Suzuki-Miyaura cross-coupling reactions in water. J. Mol. Catal. A: Chemical 2011, 337, 39-44.
143. Zheng, P.; Zhang, W. Synthesis of efficient and reusable palladium catalyst supported on pH-responsive colloid and its application to Suzuki and Heck reactions in water. J. Catal. 2007, 250, 324-330.
144. Borkowski, T.; Trzeciak, A. M.; Bukowska, A.; Tylus, W.; Kepinski, L. Palladium(0) nanoparticles formed in situ in the Suzuki-Miyaura reaction: The effect of a palladium(II) precursor. Appl. Catal. A: General 2010, 378, 83-89.
145. Song, D.; Yi, W. B. Polymethyl methacrylate micro-spheres supported palladium: A new catalyst for Heck and Suzuki reactions. J. Mol. Catal. A: Chemical 2008, 280, 20-23.
146. Yi, S. S.; Lee, D. H.; Sin, E.; Lee, Y. S. Chitosan-supported palladium(0) catalyst for microwave-prompted Suzuki cross-coupling reaction in water. Tetrahedron Lett. 2007, 48, 6771-6775.