Use of nanoparticles as catalysts in organic synthesis-cross-coupling reactions

Current Organic Chemistry

Volumn 18, Issue 3, 2014, Pages 312-326

  Sydnes, Magne O ^a  

^a UNIVERSITY OF STAVANGER   (Norway)

Author keywords

Catalysis; Copper; Cross coupling reactions; Mizoroki Heck reaction; Nanoparticles; Palladium; Sonogashira reaction; Stille reaction; Suzuki Miyaura reaction; Ullmann reaction

Indexed keywords

CATALYST SUPPORTS; COPPER; METAL NANOPARTICLES; NANOCATALYSTS; SYNTHESIS (CHEMICAL);

CATALYSTS SUPPORT; CROSS COUPLING REACTIONS; MIZOROKI-HECK REACTION; ORGANIC SYNTHESIS; SONOGASHIRA REACTIONS; STILLE REACTIONS; SUZUKI-MIYAURA; SUZUKI-MIYAURA REACTION; ULLMANN REACTION; ]+ CATALYST;

PALLADIUM;

EID: 84916243159     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/13852728113176660145     Document Type: Article

References (157)

1. Cong, H.; Porco, J. A. Jr. Chemical synthesis of complex molecules using nanoparticle catalysis. ACS Catal. 2012, 2, 65-70.
2. Felpin, F.-X.; Ayad, T.; Mitra, S. Pd/C: An old catalyst for new applications-its use for the Suzuki-Miyaura reaction. Eur. J. Org. Chem. 2006, 2679-2690.
3. Seki, M. Recent advances in Pd/C-catalyzed coupling reactions. Synthesis 2006, 2975-2992.
4. Sydnes, M. O. Recent developments in the use of palladium on solid support in organic synthesis. Curr. Org. Synth. 2011, 8, 881-891.
5. Roucoux, A.; Schulz, J.; Patin, H. Reduced transition metal colloids: a novel family of reusable catalysts? Chem. Rev. 2002, 102, 3757-3778.
6. Shiju, N. R.; Guliants, V. V. Recent developments in catalysis using nanostructured materials. Appl. Catal A: Gen. 2009, 356, 1-17.
7. Ranu, B. C.; Chattopadhyay, K.; Adak, L.; Saha, A.; Bhadra, S.; Dey, R.; Saha, D. Metal nanoparticles as efficient catalysts for organic reactions. Pure Appl. Chem. 2009, 81, 2337-2354.
8. Nanostructured Catalysts: Selective Oxidations; Hess, C., Schögl, R., Eds.; RSC Publishing: Cambridge, 2011.
9. Corbet, J.-P.; Mignani, G. Selected patented cross-coupling reaction technologies. Chem. Rev. 2006, 106, 2651-2710.
10. Fendler, J. H. Nanoparticles and Nanostructured Films: Preparation, Characterization and Applications; Wiley-VCH: Weinheim, 1998.
11. Schmid, G. In Nanoscale Materials in Chemistry, Klabunde, K. J., Ed.; Wiley-Interscience: New York, 2001; pp 15-59.
12. Vollmer, C.; Redel, E.; Abu-Shandi, K.; Thomann, R.; Manyar, H.; Hardacre, C.; Janiak, C. Microwave irradiation for the facile synthesis of transition-metal nanoparticles (NPs) in ionic liquids (ILs) from metal-carbonyl precursors and Ru-, Rh-, and Ir-NP/IL dispersions as biphasic liquid-liquid hydrogenation nanocatalysts for cyclohexene. Chem. Eur. J. 2010, 16, 3849-3858.
13. Toebes, M. L.; van Dillen, J. A.; de Jong, K. P. Synthesis of supported palladium catalysts. J. Mol. Catal. A: Chem. 2001, 173, 75-98.
14. Braunstein, P. Functional ligands and complexes for new structures, homogeneous catalysts and nanometerials. J. Organomet. Chem. 2004, 689, 3953-3967.
15. Tsuji, Y.; Fujihara, T. Homogeneous Nanosize Palladium Catalysts. Inorg. Chem. 2007, 46, 1895-1902.
16. Wu, B.; Kuang, Y.; Zhang, X.; Chen, J. Noble metal nanoparticles/carbon nanotubes nanohybrids: Synthesis and applications. Nano Today 2011, 6, 75-90.
17. Fihri, A.; Bouhrara, M.; Nekoueishahraki, B.; Basset, J.-M.; Polshettiwar, V. Nanocatalysts for Suzuki cross-coupling reactions. Chem. Soc. Rev. 2011, 40, 5181-5203.
18. Khlobystov, A. N. Carbon Nanotubes: From nano test tube to nano-reactor. ACS Nano 2011, 5, 9306-9312.
19. Lu, J.; Toy, P. H. Organic polymer supports for synthesis and for reagent and catalyst immobilization. Chem. Rev. 2009, 109, 815-838.
20. Albéniz, A. C.; Carrera, N. Polymers for Green C-C Couplings. Eur. J. Inorg. Chem. 2011, 2347-2360.
21. Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhamed, B.; Basset, J.-M. Magnetically recoverable nanocatalysts. Chem. Rev. 2011, 111, 3036-3075.
22. Chaudhuri, R. G.; Paria, S. Core/Shell Nanoparticles: classes, properties, synthesis mechanisms, characterization, and applications. Chem. Rev. 2012, 112, 2373-2433.
23. Astruc, D.; Ornelas, C.; Diallo, A. K.; Ruiz, J. Extremely efficient catalysis of carbon-carbon bond formation using “click” dendrimer-stabilized palladium nanoparticles. Molecules 2010, 15, 4947-4960.
24. Astruc, D.; Lu, F.; Aranzaes, J. R. Nanoparticles as recyclable catalysts: the frontier between homogeneous and heterogeneous catalysis. Angew. Chem. Int. Ed. 2005, 44, 7852-7872.
25. Ponce, A. A.; Klabunde, K. J. Chemical and catalytic activity of copper nanoparticles prepared via metal vapor synthesis. J. Mol. Catal. A: Chem. 2005, 225, 1-6.
26. Amali, A. J.; Rana, R. K. Stabilisation of Pd(0) on surface functionalized Fe3O4 nanoparticles: magnetically recoverable and recyclable catalyst for hydrogenation and Suzuki-Miyaura reactions. Green Chem. 2009, 11, 1781-1786.
27. Zhang, R.; Liu, J.; Li, F.; Wang, S.; Xia, C.; Sun, W. Magnetically separable and versatile pd/fe3o4 catalyst for efficient suzuki cross-coupling reaction and selective hydrogenation of nitroarenes. Chin. J. Chem. 2011, 29, 525-530.
28. Du, Q.; Zhang, W.; Ma, H.; Zheng, J.; Zhou, B.; Li, Y. Immobilized palladium on surface-modified Fe3O4/SiO2 nanoparticles: as a magnetically separable and stable recyclable high-performance catalyst for Suzuki and Heck cross-coupling reactions. Tetrahedron 2012, 68, 3577-3584.
29. Jin, M.-J.; Lee, D.-H. A practical heterogeneous catalyst for the suzuki, sonogashira, and stille coupling reactions of unreactive aryl chlorides. Angew. Chem. Int. Ed. 2010, 49, 1119-1122.
30. Bui, N. T.; Dang, T. B.; Le, H. V.; Phan, N. T. S. Suzuki reaction of aryl bromides using a phosphine-free magnetic nanoparticle-supported palladium catalyst. Chin. J. Catal. 2011, 32, 1667-1676.
31. Li, H.; Zhu, Z.; Li, H.; Li, P.; Zhou, X. Recyclable hollow Pd-Fe nanospheric catalyst for Sonogashira-, Heck-, and Ullmann-type coupling reactions of aryl halide in aqueous media. J. Colloid Interface Sci. 2010, 349, 613-619.
32. Wittmann, S.; Schätz, A.; Grass, R. N.; Stark, W. J.; Reiser, O. A recyclable nanoparticle-supported palladium catalyst for the hydroxycarbonylation of aryl halides in water. Angew. Chem. Int. Ed. 2010, 49, 1867-1870.
33. Schätz, A.; Long, T. R.; Grass, R. N.; Stark, W. J.; Hanson, P. R.; Reiser, O. Immobilization on a Nanomagnetic Co/C surface using rom polymerization: generation of a hybrid material as support for a recyclable palladium catalyst. Adv. Funct. Mater. 2010, 20, 4323-4328.
34. Planeix, J. M.; Coustel, N.; Coq, B.; Brotons, V.; Kumbhar, P. S.; Dutartre, R.; Geneste, P.; Bernier, P.; Ajayan, P. M. Application of carbon nanotubes as supports in heterogeneous catalysis. J. Am. Chem. Soc. 1994, 116, 7935-7936.
35. Serp, P.; Castillejos, E. Catalysis in carbon nanotubes. ChemCatChem 2010, 2, 41-47.
36. Nhut, J.-M.; Pesant, L.; Tessonnier, J.-P.; Winé, G.; Guille, J., Pham-Huu, C.; Ledoux, M.-J. Mesoporous carbon nanotubes for use as support in catalysis and as nanosized reactors for one-dimensional inorganic material synthesis. Appl. Catal. A: Gen. 2003, 254, 345-363.
37. Takasaki, M.; Motoyama, Y.; Higashi, K.; Yoon, S.-H.; Mochida, I.; Nagashima, H. Chemoselective hydrogenation of nitroarenes with carbon nanofiber-supported platinum and palladium nanoparticles. Org. Lett. 2008, 10, 1601-1604.
38. Neelgund, G. M.; Oki, A. Pd nanoparticles deposited on poly(lactic acid) grafted carbon nanotubes: Synthesis, characterization and application in Heck C-C coupling reaction. Appl. Catal. A: Gen. 2011, 399, 154-160.
39. Zhu, W.; Yang, Y.; Hu, S.; Xiang, G.; Xu, B.; Zhuang, J.; Wang, X. (Ni,Mg)3Si2O5(OH)4 Solid-solution nanotubes supported by sub-0.06 wt % palladium as a robust high-efficient catalyst for suzuki-miyaura crosscoupling. Inorg. Chem. 2012, 51, 6020-6031.
40. Shao, L.; Ji, W.; Dong, P.; Zeng, M.; Qi, C.; Zhang, X.-M. Coupling reactions of aromatic halides with palladium catalyst immobilized on poly(vinyl alcohol) nanofiber mats. Appl. Catal. A: Gen. 2012, 413-414, 267-272.
41. Hagelin, H.; Hedman, B.; Orabona, I.; Åkermark, T.; Åkermark, B.; Klug, C. A. Investigation of the palladium catalyzed aromatic coupling of pyridine derivatives. J. Mol. Catal. A: Chem. 2000, 164, 137-146.
42. Neal, L. M.; Hagelin-Weaver, H. E. C-H activation and C-C coupling of 4-methylpyridine using palladium supported on nanoparticle alumina. J. Mol. Catal. A: Chem. 2008, 284, 141-148.
43. Neal, L. M.; Hernandez, D.; Hagelin-Weaver, H. E. Effects of nanoparticle and porous metal oxide supports on the activity of palladium catalysts in the oxidative coupling of 4-methylpyridine. J. Mol. Catal. A: Chem. 2009, 307, 29-36.
44. Feng, Y.; Li, L.; Li, Y.; Zhao, W.; Gu, J.; Shi, J. Pd colloid grafted mesoporous silica and its extraordinarily high catalytic activity for Mizoroki-Heck reactions. J. Mol. Catal. A: Chem. 2010, 322, 50-54.
45. Polshettiwar, V.; Len, C.; Fihri, A. Silica-supported palladium: Sustainable catalysts for cross-coupling reactions. Coord. Chem. Rev. 2009, 253, 2599-2626.
46. Chikkali, S.; Gudat, D.; Mallissery, S. K. On the immobilisation of catechol phosphane palladium complexes on titania. Eur. J. Inorg. Chem. 2008, 5603-5608.
47. Majías, N.; Pleixats, R.; Shafir, A.; Medio-Simón, M.; Asensio, G. Watersoluble palladium nanoparticles: click synthesis and applications as a recyclable catalyst in suzuki cross-couplings in aqueous media. Eur. J. Org. Chem. 2010, 5090-5099.
48. Hariprasad, E.; Padhadrishnan, T. P. Palladium nanoparticle-embedded polymer thin film “dip catalyst” for suzuki-miyaura reaction. ACS Catal. 2012, 2, 1179-1186.
49. Negishi, E. A genealogy of Pd-catalyzed cross-coupling. J. Organomet. Chem. 2002, 653, 34-40.
50. 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.
51. Narayanan, R. Recent advances in noble metal nanocatalysts for suzuki and heck cross-coupling reactions. Molecules 2010, 15, 2124-2138.
52. Prechtl, M. H. G.; Scholten, J. D.; Dupont, J. Carbon-carbon cross coupling reactions in ionic liquids catalysed by palladium metal nanoparticles. Molecules 2010, 15, 3441-3461.
53. Balanta, A.; Godard, C.; Claver, C. Pd nanoparticles for C-C coupling reactions. Chem. Soc. Rev. 2011, 40, 4973-4985.
54. Jana, R.; Pathak, T. P.; Sigman, M. S. Advances in transition metal (Pd,Ni,Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners. Chem. Rev. 2011, 111, 1417-1492.
55. Pérez-Lorenzo, M. Palladium nanoparticles as efficient catalysts for suzuki cross-coupling reactions. J. Phys. Chem. Lett. 2012, 3, 167-174.
56. Chinchilla, R.; Najera, C. Recent advances in Sonogashira reactions. Chem. Soc. Rev. 2011, 40, 5084-5121.
57. Miyaura, N.; Suzuki, A. Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst. J. Chem. Soc., Chem. Commun. 1979, 866-867.
58. Miyaura, N.; Yamada, K.; Suzuki, A. A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides. Tetrahedron Lett. 1979, 20, 3437-3440.
59. Miyaura, N. Cross-coupling reaction of organoboron compounds via baseassisted transmetalation to palladium(II) complexes. J. Organomet. Chem. 2002, 653, 54-57.
60. Suzuki, A. Cross-coupling reactions via organoboranes. J. Organomet. Chem. 2002, 653, 83-90.
61. Suzuki, A. Cross-coupling reactions of organoboranes: An easy way to construct C-C Bonds (Nobel Lecture). Angew. Chem. Int. Ed. 2011, 50, 6723-6737.
62. Negishi, E. Magical power of transition metals: Past, Present, and Future (Nobel Lecture). Angew. Chem. Int. Ed. 2011, 50, 6738-6764.
63. Felpin, P.-X.; Ayad, T.; Mitra, S. Pd/C: An old catalyst for new applications-its use for the Suzuki-Miyaura reaction. Eur. J. Org. Chem. 2006, 2679-2690.
64. Yin, L.; Liebscher, J. Carbon-carbon coupling reactions catalyzed by heterogeneous palladium catalysts. Chem. Rev. 2007, 107, 133-173.
65. Poshettiwar, V.; Len, C.; Fihri, A. Silica-supported palladium: Sustainable catalysts for cross-coupling reactions. Coord. Chem. Rev. 2009, 253, 2599-2626.
66. There are discussions in the literature if Pd NPs are purely a heterogeneous catalyst or if it is a mixture of heterogeneous and homogeneous. For some relevant literature on the topic, see: a Narayanan, R; Tabor, C.; El-Sayed, M. A. Can the observed changes in the size or shape of a colloidal nanocatalyst reveal the nanocatalysis mechanism type: Homogeneous or heterogeneous. Top. Catal. 2008, 48, 60-74
67. Corma, A.; Garcia, H. Crossing the borders between homogeneous and heterogeneous catalysis: developing recoverable and reusable catalytic systems. Top. Catal. 2008, 48, 8-31.
68. Reetz, M. T.; Breinbauer, R.; Wanninger, K. Suzuki and heck reactions catalyzed by performed palladium clusters and palladium/nickel bimetallic clusters. Tetrahedron Lett. 1996, 37, 4499-4502.
69. Reetz, M. T.; Westermann, E. Phosphane-free palladium-catalyzed coupling reactions: the decisive role of Pd nanoparticles. Angew. Chem. Int. Ed. 2000, 39, 165-168.
70. Moreno-Mañas, M.; Pleixats, R. Formation of carbon-carbon bonds under catalysis by transition-metal nanoparticles. Acc. Chem. Res. 2003, 36, 638-643.
71. Calo, V.; Nacci, A.; Monopoli, A.; Montingelli, F. Pd Nanoparticles as efficient catalysts for suzuki and stille coupling reactions of aryl halides in ionic liquids. J. Org. Chem. 2005, 70, 6040-6044.
72. Venkatesan, P.; Santhanalakshmi, J. Synthesis, characterization and catalytic activity of trimetallic nanoparticles in the Suzuki C-C coupling reaction. J. Mol. Catal. A: Chem. 2010, 326, 99-106.
73. Wu, L.; Li, Z.-W.; He, Y.-M.; Fan, Q.-H. Air-Stable and highly active dendritic phosphine oxide-stabilized palladium nanoparticles: preparation, characterization and application in the carbon-carbon bond formation and hydrogenation reactions. Adv. Synth. Catal. 2008, 350, 846-862.
74. Iranopoor, N.; Firouzabadi, H.; Motevalli, S.; Talebi, M. Palladium nanoparticles supported on silicadiphenyl phosphinite (SDPP) as afficient catalyst for Mizoroki-Heck and Suzuki-Miyaura coupling reactions. J. Organomet. Chem. 2012, 708-709, 118-124.
75. Borah, B. J.; Saikia, K.; Saikia, P. P.; Barua, N. C.; Dutta, D. K. Pd0-nanoparticles stabilized by tripodal phosphine based ligands and their catalytic activities on carbon-carbon bond formation reactions. Catal. Today 2012, 198, 174-183.
76. Ornelas, C.; Ruiz, J.; Salmon, L.; Astruc, D. Sulphonated “Click” dendrimerstabilized palladium nanoparticles as highly efficient catalysts for olifin hydrogenation and suzuki coupling reactions under ambient conditions in aqueous media. Adv. Synth. Catal. 2008, 350, 837-845.
77. 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--cyclodextrincapped palladium nanoparticles: active scaffolds for efficient carbon-carbon bond forming cross-couplings in water. Adv. Synth. Catal. 2009, 351, 2411-2422.
78. M. J. Low-cost, high-surface-area MOFs. C&EN 2012, June 4.
79. Huang, Y.; Zheng, Z.; Liu, T.; Lü, J.; Lin, Z.; Li, H.; Cao, R. Palladium nanoparticles supported on amino functionalized metal-organic framework as highly active catalysts for the Suzuki-Miyaura cross-coupling reaction. Catal. Commun. 2011, 14, 27-31.
80. Kim, M.-R.; Choi, S.-H. One-step synthesis of Pd-M/ZnO (M=Ag, Cu, and Ni) Catalysts by g-Irradiation and their use in hydrogenation and suzuki reaction. J. Nanomat. 2009, Article ID 302919.
81. Martínez, M.; Ocampo, R.; Rios, L. A.; Ramírez, A.; Giraldo, O. Palladium nanoparticles supported on layered hydroxide salts and their use in carboncarbon coupling organic reactions. J. Braz. Chem. Soc. 2011, 22, 2322-2329.
82. Park, J. C.; Heo, E.; Kim, A.; Kim, M.; Park, K. H.; Song, H. Extreamely active pd@psio2 yolk-shell nanocatalysts for suzuki coupling reaction of aryl halides. J. Phys. Chem. C 2011, 115, 15772-15777.
83. Kim, M.; Heo, E.; Kim, A.; Park, J. C.; Song, H.; Park, K. H. Synthesis of Pd/SiO2 nanobeads for use in suzuki coupling reactions by reverse micelle sol-gel process. Catal. Lett. 2012, 142, 588-593.
84. Scheuermann, G. M.; Rumi, L.; Steurer, P.; Bannwarth, W.; Mülhaupt, R. Palladium nanoparticles on graphite oxide and its functionalized graphene derivatives as highly active catalysts for the suzuki-miyaura coupling reaction. J. Am. Chem. Soc. 2009, 131, 8262-8270.
85. Li, Y.; Fan, X.; Qi, J.; Ji, J.; Wang, S.; Zhang, G.; Zhang, F. Palladium nanoparticle-graphene hybrids as active catalysts for the suzuki reaction. Nano Res. 2010, 3, 429-437.
86. Siamaki, A. R.; Khder, A. E. R. S.; Abdelsayed, V.; El-Shall, M. S.; Gupton, B. F. Microwave-assisted synthesis of palladium nanoparticles supported on graphene: a highly active and recyclable catalyst for carbon-carbon crosscoupling reactions. J. Catal. 2011, 279, 1-11.
87. Rumi, L.; Scheuermann, G. M.; Mülhaupt, R.; Bannwarth, W. Palladium nanoparticles on graphit oxide as catalyst for suzuki-miyaura, mizoroki-heck, and sonogashira reactions. Helv. Chim. Acta 2011, 94, 966-976.
88. Moussa, S.; Siamaki, A. R.; Gupton, B. F.; El-Shall, M. S. Pd-Partially reduced graphene oxide catalysts (Pd/PRGO): Laser synthesis of pd nanoparticles supported on prgo nanosheets for carbon-carbon cross coupling reactions. ACS Catal. 2012, 2, 145-154.
89. Kim, S.-J.; Oh, S.-D.; Lee, S.; Choi, S.-H. Radiolytic synthesis of Pd-M (M = Ag, Ni, and Cu)/C catalyst and their use in Suzuki-type and Heck-type reaction. J. Ind. Eng. Chem. 2008, 14, 449-456.
90. Léger, B.; Nowicki, A.; Roucoux, A.; Rolland, J.-P. Competitive hydrogenation/dehalogenation of halogenoarenes with surfactant-stabilized aqueous suspensions of rhodium and palladium colloids: A major effect of the metal nature. J. Mol. Catal. A: Chem. 2007, 266, 221-225.
91. Denicourt-Nowicki, A.; Romagné, M.-L.; Roucoux, A. N-(2-hydroxyethyl)ammonium derivatives as protective agents for Pd(0) nanocolloids and catalytic investigation in Suzuki reactions in aqueous media. Catal. Commoun. 2008, 10, 68-70.
92. Ornelas, C.; Diallo, A. K.; Ruiz, J.; Astruc, D. “Click” polymer-supported palladium nanoparticles as highly efficient catalysts for olefin hydrogenation and suzuki coupling reactions under ambient conditions. Adv. Synth. Catal. 2009, 351, 2147-2154.
93. Durap, F.; Metin, Ö.; Aydemir, M.; Özkar, S. New route to synthesis of PVP-stabilized palladium (0) nanoclusters and their enhanced catalytic activity in Heck and Suzuki cross-coupling reactions. Appl. Organomet. Chem. 2009, 23, 498-503.
94. Liu, S.; Zhou, Q.; Jiang, H. Water soluble starch stabilized palladium nanoparticle: efficient catalyst for miyaura-suzuki coupling reaction. Chin. J. Chem. 2010, 28, 589-593.
95. Chtchigrovsky, M.; Lin, Y.; Ouchaou, K.: Chaumontet, M.; Robitzer, M.; Quignard, F.; Taran, F. Dramatic effect of the gelling cation on the catalytic performances of alginate-supported palladium nanoparticles for the suzukimiyaura reaction. Chem. Mater. 2012, 24, 1505-1510.
96. Kashin, A. N.; Beletskaya, I. P. Suzuki-miyaura reaction in water, catalyzed by palladium nanoparticles stabilized by pluronic F68 triblock copolymer. Russ. J. Org. Chem. 2011, 47, 475-479.
97. Ogasawara, S.; Kato, S. Palladium nanoparticles captured in macroporous polymers: a tailor-made catalyst for heterogeneous carbon cross-coupling reactions. J. Am. Chem. Soc. 2010, 132, 4608-4613.
98. Kashin, A. N.; Panchuk, D. A.; Yarysheva, L. M.; Volynskii, A. L.; Beletskaya, I. P. Preparation of an active suzuki-miyaura catalyst from nanoparticles obtained by deposition of palladium onto a ployvinyl alcohol support. Russ. J. Org. Chem. 2011, 47, 48-53.
99. Tamami, B.; Farjadian, F. Synthesis and application of polyvinylpyridinegrafted silica containing palladium nanoparticles as a new heterogeneous catalyst for heck and suzuki coupling reactions. J. Iran Chem. Soc. 2011, 8, S77-S88.
100. Kaur, H.; Shah, D.; Pal, U. Resin encapsulated palladium nanoparticles: An efficient and robust catalyst for microwave enhanced Suzuki-Miyaura coupling. Catal. Commun. 2011, 12, 1384-1388.
101. [100] Tamami, B.; Allahyari, H.; Farjadian, F.; Ghasemi, S. Synthesis and application of poly(N-vinylimidazole) grafted silica-containing palladium nanoparticles as a new re-cyclable catalyst for heck, sonogashira and suzuki coupling reactions. Iran. Polym. J. 2011, 20, 699-712.
102. [101] Tamami, B.; Ghasemi, S. Palladium nanoparticles supported on modified crosslinked polyacrylamide containing phosphinite ligand: A novel and efficient heterogeneous catalyst for carbon-carbon cross-coupling reactions. J. Mol. Catal. A: Chem. 2010, 322, 98-105.
103. [102] Zhang, D.; Zhou, C.; Wang, R. Palladium nanoparticles immobilized by click ionic copolymers: Efficient and recyclable catalysts for Suzuki-Miyaura cross-coupling reaction in water. Catal. Commun. 2012, 22, 83-88.
104. [103] Chandrasekhar, V.; Narayanan, R. S.; Thilager, P. Organostannoxanesupported palladium nanoparticles. highly efficient catalysts for suzukicoupling reactions. Organometallics 2009, 28, 5883-5888.
105. [104] Zhou, C.; Wang, J.; Li, L.; Wang, R.; Hong, M. A palladium chelating complex of ionic water-soluble nitrogen-containing ligand: the efficient precatalyst for Suzuki-Miyaura reaction in water. Green Chem. 2011, 13, 2100-2106.
106. [105] Costa, N. J. S.; Kiyohara, P. K.; Monteiro, A. L.; Coppel, Y.; Philippot, K.; Rossi, L. M. A single-step procedure for the preparation of palladium nanoparticles and a phosphine-functionalized suppoart as catalyst for Suzuki cross-coupling reactions. J. Catal. 2010, 276, 382-389.
107. [106] Liang, L.; Diallo, A. K.; Salmon, L.; Ruiz, J.; Astruc, D. Catalysis of C-C cross-coupling reactions in aqueous solvent by bis-and tris(ferrocenyltriazolylmethyul)arene--cyclodextrin-stabilized Pd0 nanoparticles. Eur. J. Inorg. Chem. 2012, 2950-2958.
108. [107] Mizoroki, T.; Mori, K.; Ozaki, A. Arylation of olefin with aryl iodide catalyzed by palladium. Bull. Chem. Soc. Jpn. 1971, 44, 581.
109. [108] Heck, R. F.; Nolley, J. P. Jr. Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J. Org. Chem. 1972, 37, 2320-2322.
110. [109] Mori, K.; Mizoroki, T.; Ozaki, A. Arylation of olefin with iodobenzene catalyzed by palladium. Bull. Chem. Soc. Jpn. 1973, 46, 1505-1508.
111. [110] Heck, R. F. Cobalt and palladium reagents in organic synthesis: The beginning. Synlett 2006, 2855-2860.
112. [111] Wan, Y.; Wang, H.; Zhao, Q.; Klingstedt, M.; Terasaki, O.; Zhao, D. Ordered mesoporous Pd/silica-carbon as a highly active heterogeneous catalyst for coupling reaction of chlorobenzene in aqueous media. J. Am. Chem. Soc. 2009, 131, 4541-4550.
113. [112] Monopoli, A.; Nacci, A.; Calò, V.; Ciminal, F.; Cotugno, P.; Mangone, A.; Giannossa, L. C.; Azzone, P.; Cioffi, N. Palladium/Zirconium oxide nanocomposite as a highly recyclable catalyst for c-c coupling reactions in water. Molecules 2010, 15, 4511-4525.
114. [113] Zhou, P.; Wang, H.; Yang, J.; Tang, J.; Sun, D.; Tang, W. Bacteria cellulose nanofibers supported palladium (0) nanocomposite and its catalysis evaluation in heck reaction. Ind. Eng. Chem. Res. 2012, 51, 5743-5748.
115. [114] Kalbasi, R. J.; Mosaddegh, N.; Abbaspourrad, A. Palladium nanoparticles supported on a poly(N-vinyl-2-pyrrolidone)-modified mesoporous carbon nanocage as a novel heterogeneous catalyst for the Heck reaction in water. Tetrahedron Lett. 2012, 53, 3763-3766.
116. [115] Kalbasi, R. J.; Mosaddegh, N.; Abbaspourrad, A. A novel catalyst containing palladium nanoparticles supported on poly(2-hydroxyethyl methacrylate)/CMK-1: Synthesis, charactherization and comparison with mesoporous silica nanocomposite. Appl. Catal. A: Gen. 2012, 423-424, 78-90.
117. [116] Ren, N.; Yang, Y.-H.; Zhang, Y.-H.; Wang, Q.-R.; Tang, Y. Heck coupling in zeolitic microcapsular reactor: A test for encaged quasi-homogeneous catalysis. J. Catal. 2007, 246, 215-222.
118. [117] Hashmatpour, F.; Abazari, R.; Balalaie, S. Preparation of monometallic (Pd, Ag) and bimetallic (Pd/Ag, Pd/Ni, Pd/Cu) nanoparticles via reversed miscelles and their us in the Heck reaction. Tetrahedron 2012, 68, 3001-3011.
119. [118] Nishiwaki, N.; Shimoda, M.; Tsukamoto, S. Green chemical catalyst supported on S-terminated GaN(0001). Appl. Phys. Express 2009, 2, 051002.
120. [119] Konishi, T.; Ueta, Y.; Hirayama, M.; Nishiwaki, N.; Tsukamoto, S. Stermination effects for the catalytic activities of Pd on GaN(0001) surfaces. Appl. Surf. Sci. 2012, 258, 8334-8337.
121. [120] Demel, J.; Čejka, J.; Štěpnička, P. The use of palladium nanoparticles supported on MCM-41 mesoporous molecular sieves in Heck reaction: A comparison of basic and neutral supports. J. Mol. Catal. A: Chem. 2007, 274, 127-132.
122. [121] Sonogashira, K. Development of Pd-Cu catalyzed cross-coupling of terminal acetylenes with sp2-carbon halides. J. Organomet. Chem. 2002, 653, 46-49.
123. [122] Cassar, L. J. Synthesis of aryl-and vinyl-substituted acetylene derivatives by the use of nickel and palladium complexes. J. Organomet. Chem. 1975, 93, 253-257.
124. [123] Dieck, H. A.; Heck, F. R. Palladium catalyzed synthesis of aryl, heterocyclic and vinylic acetylene derivatives. J. Organomet. Chem. 1975, 93, 259-263.
125. [124] Sonogashira, K.; Tohda, Y.; Hagihara, N. A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromalkenes, iodoarenes and bromopyridines. Tetrahedron Lett. 1975, 16, 4467-4470.
126. [125] Sonogashira, K. Cross-coupling reactions to sp carbon atoms. In Metal-Catalyzed Cross-Coupling Reactions, Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 203-229.
127. [126] Sonogashira, K. Palladium-catalyzed alkynylation. In Handbook of Organopalladium Chemistry for Organic Synthesis, Negishi, E., Ed.; John Wiley & Sons: Hoboken, 2002, pp 493-529.
128. [127] Athilakshmi, J.; Ramanathan, S.; Chaned, D. K. Facile synthesis of palladium nanoclusters and their catalytic activity in Sonogashira coupling reactions. Tetrahedron Lett. 2008, 49, 5286-5288.
129. [128] Venkatesan, P.; Santhanalakshmi, J. Designed synthesis of Au/Ag/Pd trimetallic nanoparticle-based catalysts for sonogashira coupling reactions. Langmuir 2010, 26, 12225-12229.
130. [129] Gao, S.; Zhao, N.; Shu, M.; Che, S. Palladium nanoparticles supported on MOF-5: A highly active catalyst for a ligand-and copper-free Sonogashira coupling reaction. Appl. Catal. A: Gen. 2010, 388, 196-201.
131. [130] Ullmann, F.; Bielecki, J. Ueber synthesen in der biphenylreihe. Berichte 1901, 34, 2174-2185.
132. [131] Fanta, P. E. The ullmann synthesis of biaryls. Synthesis 1974, 9-21.
133. [132] Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Aryl-Aryl bond formation one century after the discovery of the ullmann reaction. Chem. Rev. 2002, 102, 1359-1469.
134. [133] Beletskaya, I. P.; Cheprakov, A. V. Copper in cross-coupling reactions The post-Ullmann chemistry. Coord. Chem. Rev. 2004, 248, 2337-2364.
135. [134] Monnier, F.; Taillefer, M. Catalytic C-C-, C-N, and C-O Ullmann-Type coupling reactions: Copper makes a difference. Angew. Chem. Int. Ed. 2008, 47, 3096-3099.
136. [135] Evano, G.; Blanchard, N.; Toumi, M. Copper-Mediated coupling reactions and their applications in natural products and designed biomolecules synthesis. Chem. Rev. 2008, 108, 3054-3131.
137. [136] Monnier, F.; Taillefer, M. Catalytic C-C, C-N, and C-O Ullmann-Type coupling reactions. Angew. Chem. Int. Ed. 2009, 48, 6954-6971.
138. [137] Dhas, N. A.; Raj, C. P.; Gedanken, A. Synthesis, Characterization, and properties of metallic copper nanoparticles. Chem. Mater. 1998, 10, 1446-1452.
139. [138] Samim, M.; Kaushik, N. K.; Maitra, M. Effect of size of copper nanoparticles on its catalytic behaviour in Ullmann reaction. Bull. Mater. Sci. 2007, 30, 535-540.
140. [139] Santra, S.; Ranjan, P.; Mandal, S. K.; Ghorai, P. K. Living nanocatalyst for effective synthesis of symmetrical biaryls. Inorg. Chim. Acta 2011, 372, 47-52.
141. [140] Pachón, L. D.; Elsevier, C. J.; Rothenberg, G. Electroreductive palladiumcatalysed ullmann reactions in ionic liquids: scope and mechanism. Adv. Synth. Catal. 2006, 348, 1705-1710.
142. [141] Calò, V.; Nacci, A.; Monopoli, A.; Cotugno, P. Palladium-Nanoparticle-Catalysed ullmann reactions in ionic liquids with aldehydes as the reductants: Scope and mechanism. Chem. Eur. J. 2009, 15, 1272-1279.
143. [142] Qi, G.; Zhang, Y.-H. Synthesis of Ni@Au core-shell nanoparticles and its applications in ullmann reaction as a synergistic catalyst. Chin. J. Struct. Chem. 2011, 30, 1122-1126.
144. [143] Yuan, B.; Pan, Y.; Li, Y.; Yin, B.; Jiang, H. A Highly active heterogeneous palladium catalyst for the suzuki-miyaura and ullmann coupling reactions of aryl chlorides in aqueous media. Angew. Chem. Int. Ed. 2010, 49, 4054-4058.
145. [144] Milstein, D.; Stille, J. K. A general, selective, and facile method for ketone synthesis from acid chlorides and organotin compound catalyzed by palladium. J. Am. Chem. Soc. 1978, 100, 3636-3638.
146. [145] Milstein, D.; Stille, J. K. Palladium-catalyzed coupling of tetraorganotin compounds with aryl and benzyl halides. Synthetic utility and mechanism. J. Am. Chem. Soc. 1979, 101, 4992-4998.
147. [146] Stille, J. K. The Palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles. Angew. Chem. Int. Ed. 1986, 25, 508-524.
148. [147] Li, J.H.; Tang, B.-X.; Tao, L.-M.; Xie, Y.-X.; Liang, Y.; Zhang, M.-B. Reusable copper-catalyzed cross-coupling reactions of aryl halides with organotins in inexpensive ionic liquids. J. Org. Chem. 2006, 71, 7488-7490.
149. [148] Bernechea, M.; de Jesús, E.; López-Mardomingo, C.; Terreros, P. Dendrimer-encapsulated pd nanoparticles versus palladium acetate as catalytic precursors in the stille reaction in water. Inorg. Chem. 2009, 48, 4491-4496.
150. [149] Corma, A.; Garcia, H. Crossing the borders between homogeneous and heterogeneous catalysis: developing recoverable and reusable catalytic systems. Top. Catal. 2008, 48, 8-31.
151. [150] Narayanan, R.; Tabor, C.; El-Sayed, M. A. Can the observed changes in the size or shape of a colloidal nanocatalyst reveal the nanocatalysis mechanism type: Homogeneous or heterogeneous? Top. Catal. 2008, 48, 60-74.
152. [151] Schmidt, A. F.; Kurokhtina, A. A.; Larina, E. V. Simple kinetic method for distinguishing between homogeneous and heterogeneous mechanisms of catalysis, illustrated by the example of “Ligand-Free” suzuki and heck reactions of aryl iodides and aryl bromides. Kinet. Catal. 2012, 53, 84-90.
153. [152] Gruber, A. S.; Pozebon, D.; Monteiro, A. L.; Dupont, J. On the use of phosphine-free PdCl2(SEt2)2 complex as catalyst precursor for the Heck reaction. Tetrahedron Lett. 2001, 42, 7345-7348.
154. [153] Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; William, V. A.; Granados, P.; Singer, R. D. a Reassessment of the transition-metal free suzuki-type coupling methodology. J. Org. Chem. 2005, 70, 161-168.
155. [154] Davies, I. W.; Matty, L.; Hughes, D. L.; Reider, P. J. Are heterogeneous catalysts precursors to homogeneous catalysts. J. Am. Chem. Soc. 2001, 123, 10139-10140.
156. [155] Lipshytz, B. H.; Tasler, S.; Chrisman, W.; Spliethoff, B.; Tesche, B. On the nature of the ‘Heterogeneous’ catalyst: Nickel-on-charcoal. J. Org. Chem. 2003, 68, 1177-1189.
157. [156] 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. Suzuki-miyaura cross-coupling with quasi-heterogeneous palladium. Adv. Synth. Catal. 2003, 345, 931-935.