Pd(0) nanoparticles (NPs) as catalysts in cross-coupling reactions and the homogeneous vs. heterogeneous debate

Organometallic Chemistry

Volumn 40, Issue , 2016, Pages 33-53

  Muimhneacháin, Eoin Ó ^a   McGlacken, Gerard P ^a  

^a UNIVERSITY COLLEGE CORK   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84952943453     PISSN: 03010074     EISSN: None     Source Type: Book Series    
DOI: 10.1039/9781782623960-00033     Document Type: Article

References (113)

1. (a) A. de Mejere and F. Diederich, Metal-Catalysed Cross-Coupling Reacions, Wiley-VCH, Weinheim, Germany, 2004;
2. (b) K. C. Nicolaou, P. G. Bulger and D. Sarlah, Angew. Chem., Int. Ed., 2005, 44, 4442.
3. K. Kohler, M. Wagner and L. Djakovitch, Catal. Today, 2001, 66, 105.
4. Note for Guidance on Specification Limits for Residues of Metal Catalysts, In The European Agency for the Evaluation of Medicinal Products, Evaluation of Medicines for Human Use, London, 2002.
5. V. Farina, Adv. Synth. Catal., 2004, 346, 1553.
6. (a) D. Alberico, M. E. Scott and M. Lautens, Chem. Rev., 2007, 107, 174;
7. (b) G. P. McGlacken and L. Bateman, Chem. Soc. Rev., 2009, 38, 2447;
8. (c) P. Thansandote and M. Lautens, Chem. - Eur. J., 2009, 15, 5874;
9. (d) L. Ackermann, R. Vicente and A. R. Kapdi, Angew. Chem., Int. Ed., 2009, 48, 9792.
10. A. Balanta, C. Godard and C. Claver, Chem. Soc. Rev., 2011, 40, 4973.
11. Nanoparticles and Catalysis, ed. D. Astruc, Wiley-VCH, Weinheim, Germany, 2008.
12. Controlled Nanofabrication: Advances and Applications, ed. L. Ru-Shi, Pan Stanford Publishing Pte Ltd., Singapore, 2013.
13. J. Cookson, Platinum Met. Rev., 2012, 56, 83-98.
14. J. A. Widegren and R. G. Finke, J. Mol. Catal. A: Chem., 2003, 191, 187.
15. (a) H. Ramezani-Dakhel, P. A. Mirau, R. R. Naik, M. R. Knecht and H. Heinz, Phys. Chem. Chem. Phys., 2013, 15, 5488;
16. (b) J. Cookson, Platinum Met. Rev., 2012, 56, 83.
17. (a) R. A. Sperling and W. J. Parak, Philos. Trans. R. Soc., A, 2010, 368, 1333;
18. (b) Metal-Catalyzed Reactions in Water, Wiley-VCH, Weinheim, Germany, 2013.
19. J. Le Bars, U. Specht, J. S. Bradley and D. G. Blackmond, Langmuir, 1999, 15, 7621.
20. J. M. J. Fréchet and D. A. Tomalia, Dendrimers and Other Dendritic Polymers, J. Wiley & Sons, 2001.
21. G. M. Dykes, J. Chem. Technol. Biotechnol., 2001, 76, 903.
22. R. M. Crooks, M. Zhao, L. Sun, V. Chechik and L. K. Yeung, Acc. Chem. Res., 2000, 34, 181.
23. (a) M. Zhao, H. Tokuhisa and R. M. Crooks, Angew. Chem., Int. Ed. Engl., 1997, 36, 2596;
24. (b) M. Wells and R. M. Crooks, J. Am. Chem. Soc., 1996, 118, 3988.
25. (a) V. Chechik and R. M. Crooks, J. Am. Chem. Soc., 2000, 122, 1243;
26. (b) H. Tokuhisa and R. M. Crooks, Langmuir, 1997, 13, 5608.
27. M. T. Reetz, R. Branbauer and K. Wanninger, Tetrahedron Lett., 1996, 37, 4499.
28. (a) Y. Li, X. M. Hong, D. M. Collard and M. A. El-Sayed, Org. Lett., 2000, 2, 2385;
29. (b) Y. Liand and M. A. El-Sayed, J. Phys. Chem. B, 2001, 105, 8938;
30. (c) R. Narayanan and M. A. El-Sayed, J. Phys. Chem. B, 2004, 108, 8572;
31. (d) R. Narayanan and M. A. El-Sayed, Langmuir, 2005, 21, 2027;
32. (e) R. Narayanan and M. A. El-Sayed, J. Catal., 2005, 234, 348.
33. (a) T. Y. Zhang, Palladium Catalysts Immobilized on Polymeric Supports, in Handbook of Organopalladium Chemistry for Organic Synthesis, John Wiley & Sons, Inc., New York, USA, 2003;
34. (b) J. Guerra and M. A. Herrero, Nanoscale, 2010, 2, 1390.
35. D. Sanhes, E. Raluy, S. Retory, N. Saffon, E. Teuma and M. Gomez, Dalton Trans., 2010, 39, 9719.
36. V. Calo, A. Nacci, A. Monopoli and F. Montingelli, J. Org. Chem., 2005, 70, 6040.
37. C. Deraedt and D. Astruc, Acc. Chem. Res., 2014, 47, 494.
38. (a) A. H. M. de Vries, J. M. C. A. Mulders, J. H. M. Mommers and H. W. J. Henderickx, Org. Lett., 2003, 5, 3285;
39. (b) M. T. Reetz and J. G. de Vries, Chem. Commun., 2004, 14, 1559.
40. I. P. Beletskaya and A. V. Cheprakov, Chem. Rev., 2000, 100, 3009.
41. F. Zhao, M. Shirai and M. Arai, J. Mol. Catal. A: Chem., 2000, 154, 39.
42. (a) N. E. Leadbeater, Nat. Chem., 2010, 2, 1007;
43. (b) N. E. Leadbeater and M. Marco, Angew. Chem., Int. Ed., 2003, 42, 1407;
44. (c) N. E. Leadbeater and M. Marco, J. Org. Chem., 2003, 68, 5660;
45. (d) N. E. Leadbeater, M. Marco and B. J. Tominack, Org. Lett., 2003, 5, 3919;
46. (e) C. J. Li, Agnew. Chem., Int. Ed., 2003, 115, 5004;
47. (f) R. K. Arvela, N. E. Leadbeater, M. S. Sangi, V. A. Williams, P. Granados and R. D. Singer, J. Org. Chem., 2005, 70, 161.
48. (a) C.-L. Sun, H. Li, D.-G. Yu, M. Yu, X. Zhou, X.-Y. Lu, K. Huang, S.-F. Zheng, B.-J. Li and Z.-J. Shi, Nat. Chem., 2010, 2, 1044;
49. (b) W. Liu, H. Cao, H. Zhang, H. Zhang, K. H. Chung, C. He, H. Wang, F. Y. Kwong and A. Lei, J. Am. Chem. Soc., 2010, 132, 16737.
50. J. G. de Vries, Dalton Trans., 2006, 421.
51. (a) R. F. Heck, J. Am. Chem. Soc., 1969, 91, 6707;
52. (b) Y. Fujiwara, I. Noritani, S. Danno, R. Asano and S. Teranishi, J. Am. Chem. Soc., 1969, 91, 7166.
53. T. Jeffery, J. Chem. Soc., Chem. Commun., 1984, 19, 1287.
54. J. Kiwi and M. Graetzel, J. Am. Chem. Soc., 1979, 101, 7214.
55. M. T. Reetz and M. Maase, Adv. Mater., 1999, 11, 773.
56. M. T. Reetz and G. Lohmer, Chem. Commun., 1996, 16, 1921.
57. M. T. Reetz and E. Westermann, Angew. Chem., Int. Ed., 2000, 39, 165.
58. M. Nowotny, U. Hanefeld, H. van Koningsveld and T. Maschmeyer, Chem. Commun., 2000, 1877.
59. T. Rosner, J. Le Bars, A. Pfaltz and D. G. Blackmond, J. Am. Chem. Soc., 2001, 123, 1848.
60. (a) S. S. Zalesskiy and V. P. Ananikov, Organometallics, 2012, 31, 2302;
61. (b) A. S. Kashin and V. P. Ananikov, J. Org. Chem., 2013, 78, 11117;
62. (c) L. A. Adrio, B. N. Nguyen, G. Guilera, A. G. Livingston and K. K. Hii, Catal.: Sci. Technol., 2012, 2, 316.
63. M. T. Reetz, R. Breinbauer, P. Wedemann and P. Binger, Tetrahedron, 1998, 54, 1233.
64. V. P. Ananikov and I. P. Beletskaya, Organometallics, 2012, 31, 1595.
65. J. A. Widegren and R. G. Finke, J. Mol. Catal. A: Chem., 2003, 198, 317.
66. (a) M. B. Thatagar, G. Ten Elshof and G. Rothenberg, Angew. Chem., Int. Ed., 2006, 45, 2886;
67. (b) A. V. Gaikwad, A. Holuigue, M. B. Thathagar, J. E. ten Elshof and G. Rothenberg, Chem. - Eur. J., 2007, 13, 6908.
68. L. Yin and J. Liebscher, Chem. Rev., 2007, 107, 133.
69. K. Köhler, R. G. Heidenreich, J. G. E. Krauter and J. Pietsch, Chem. - Eur. J., 2002, 3, 622.
70. C. Rossy, J. Majimel, M. T. Delapierre, E. Fouquet and F.-X. Felpin, Appl. Catal., A, 2014, 482, 157.
71. (a) P. J. Ellis, I. J. S. Fairlamb, S. F. J. Hackett, K. Wilson and A. F. Lee, Angew. Chem., Int. Ed., 2010, 49, 1820;
72. (b) A. F. Lee, P. J. Ellis, I. J. S. Fairlamb and K. Wilson, Dalton Trans., 2010, 39, 10473.
73. P.-P. Fang, A. Jutand, Z.-Q. Tian and C. Amatore, Angew. Chem., Int. Ed., 2011, 50, 12184.
74. G. Collins, M. Schmidt, C. O'Dwyer, J. D. Holmes and G. P. McGlacken, Angew. Chem., Int. Ed., 2014, 53, 4142.
75. (a) R. Narayanan and M. A. El-Sayed, Langmuir, 2005, 21, 2027;
76. (b) R. Narayanan and M. A. El-Sayed, J. Phys. Chem. B, 2005, 109, 12663.
77. (a) J. J. Davis, C. B. Bagshaw, K. L. Busuttil, Y. Hanyu and K. S. Coleman, J. Am. Chem. Soc., 2006, 128, 14135;
78. (b) J. J. Davis, K. S. Coleman, K. L. Busuttil and C. B. Bagshaw, J. Am. Chem. Soc., 2005, 127, 13082;
79. (c) P. J. Ellis, I. J. S. Fairlamb, S. F. J. Hackett, K. Wilson and A. F. Lee, Angew. Chem., Int. Ed., 2010, 49, 1820.
80. J. Xu, A. R. Wilson, A. R. Rathmell, J. Howe, M. Chi and B. J. Wiley, ACS Nano, 2011, 5, 6119.
81. R. G. Heidenreich, J. G. E. Krauter, J. Pietsch and K. Köhler, J. Mol. Catal. A: Chem., 2002, 182-183, 499.
82. W. Han, C. Liu and Z. Jin, Adv. Synth. Catal., 2008, 350, 501.
83. R. Tatumi, T. Akita and H. Fujihara, Chem. Commun., 2006, 3349.
84. K. Sawai, R. Tatumi, T. Nakahodo and H. Fujihara, Angew. Chem., Int. Ed., 2008, 47, 6917.
85. M. Parisien, D. Valette and K. Fagnou, J. Org. Chem., 2005, 70, 7578.
86. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara and J.-M. Basset, Chem. Rev., 2011, 111, 3036.
87. J. A. Coggan, N.-X. Hu, H. B. Goodbrand and T. P. Bender, Pilsbury Winthrop Shaw Pittman, LLP 2006, US 2006/025303 A1.
88. M. Moreno-Mañas, R. Pleixats and S. Villarroya, Organometallics, 2001, 20, 4524.
89. J. D. Senra, L. F. B. Malta, M. E. H. M. da Costa, R. C. Michel, L. C. S. Aguiar, A. B. C. Simas and O. A. C. Antunes, Adv. Synth. Catal., 2009, 351, 2411.
90. (a) G. Liu, M. Hou, J. Song, T. Jiang, H. Fan, Z. Zhang and B. Han, Green Chem., 2010, 12, 65;
91. (b) R. Xing, Y. Liu, H. Wu, X. Li, M. He and P. Wu, Chem. Commun., 2008, 47, 6297.
92. T. Borkowski, W. Zawartka, P. Pospiech, U. Mizerska, A. M. Trzeciak, M. Cypryk and W. Tylus, J. Catal., 2011, 282, 270.
93. E. Mieczyńska, T. Borkowski, M. Cypryk, P. Pospiech and A. M. Trzeciak, Appl. Catal., A, 2014, 470, 24.
94. K. Mennecke and A. Kirschning, Beilstein J. Org. Chem., 2009, 5, 21.
95. C. K. Y. Lee, A. B. Holmes, S. V. Ley, I. F. McConvey, B. Al-Duri, G. A. Leeke, R. C. D. Santos and J. P. K. Seville, Chem. Commun., 2005, 16, 2175.
96. T. Noel and S. L. Buchwald, Chem. Soc. Rev., 2011, 40, 5010.
97. S. Klingelhöfer, W. Heitz, A. Greiner, S. Oestreich, S. Förster and M. Antonietti, J. Am. Chem. Soc., 1997, 119, 10116.
98. A. M. Caporusso, P. Innocenti, L. A. Aronica, G. Vitulli, R. Gallina, A. Biffis, M. Zecca and B. Corain, J. Catal., 2005, 234.
99. E. H. Rahim, F. S. Kamounah, J. Frederiksen and J. B. Christensen, Nano Lett., 2001, 1, 499.
100. S. Sobhani and Z. Pakdin-Parizi, Appl. Catal., A, 2014, 479, 112.
101. E. C. Keske, O. V. Zenkina, R. Wang and C. M. Crudden, Organometallics, 2012, 31, 6215.
102. A. Boffi, S. Cacchi, P. Ceci, R. Cirilli, G. Fabrizi, A. Prastaro, S. Niembro, A. Shafir and A. Vallribera, ChemCatChem, 2011, 3, 347.
103. (a) E. Hariprasad and T. P. Radhakrishnan, ACS Catal., 2012, 2, 1179;
104. (b) E. Hariprasad and T. P. Radhakrishnan, Chem. - Eur. J., 2010, 16, 14378.
105. L. Li, J. Wang, T. Wu and R. Wang, Chem. - Eur. J., 2012, 18, 7842.
106. A. Khazaei, S. Rahmati and S. Saednia, Catal. Commun., 2013, 37, 9.
107. L. A. Aronica, A. M. Caporusso, G. Tuci, C. Evangelisti, M. Manzoli, M. Botavina and G. Martra, Appl. Catal., A, 2014, 480, 1.
108. (a) J. Hassan, M. Sévignon, C. Gozzi, E. Schulz and M. Lemaire, Chem. Rev., 2002, 102, 1359;
109. (b) C. C. C. Johansson Seechurn, M. O. Kitching, T. J. Colacot and V. Snieckus, Angew. Chem., Int. Ed., 2012, 51, 5062.
110. Y. Huang, Z. Lin and R. Cao, Chem. - Eur. J., 2011, 17, 12706.
111. J. Lee, J. Chung, S. M. Byun, B. M. Kim and C. Lee, Tetrahedron, 2013, 69, 5660.
112. D.-T. D. Tang, K. D. Collins and F. Glorius, J. Am. Chem. Soc., 2013, 135, 7450.
113. L. Adak, S. Bhadra and B. C. Ranu, Tetrahedron Lett., 2010, 51, 3811.