Macrocyclic palladium(II) complexes in C-C coupling reactions: Efficient catalysis by controlled temporary release of active species

Advanced Synthesis and Catalysis

Volumn 352, Issue 13, 2010, Pages 2263-2274

  Röhlich, Christoph ^a   Köhler, Klaus ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

C c coupling; Homogeneous catalysis; Macrocyclic ligands; Palladium

Indexed keywords

EID: 77956896871     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000458     Document Type: Article

References (62)

1. N. Miyaura, Adv. Synth. Catal. 2004, 346, 1522.
2. A. Eisenstadt, D. J. Ager, in: Fine Chemicals through Heterogeneous Catalysis, (Eds. : R. A. Sheldon, H. van Bekkum), Wiley-VCH, Weinheim, New York, 2001, p 576.
3. A. Zapf, M. Beller, Top. Catal. 2002, 19, 101.
4. E. Negishi, Bull. Chem. Soc. Jpn. 2007, 80, 233.
5. a) R. Martin, S. L. Buchwald, Acc. Chem. Res. 2008, 41, 1461;
6. b) S. R. Dubbaka, Synlett 2005, 4, 709;
7. c) L. Ackermann, R. Born, X H. Spatz, A. Althammer, C. J. Gschrei, Pure Appl. Chem. 2006, 78, 209.
8. a) E. A. Kantchev, C. J. O'Brien, M. G. Organ, Angew. Chem. 2007, 119, 2824;
9. Angew. Chem. Int. Ed. 2007, 46, 2768;
10. b)W. A. Herrmann, K. Oefele, D. von Preysing, S. K. Schneider, J. Organomet. Chem. 2003, 687, 229;
11. c) S. Sakaguchi, K. S. Yoo, J. O'Neill, J. H. Lee, T. Stewart, K. W. Jung, Angew. Chem. 2008, 120, 9466;
12. Angew. Chem. Int. Ed. 2008, 47, 9326;
13. d) K. S. Yoo, C. H. Yoon, K. W. Jung, J. Am. Chem. Soc. 2006, 128, 16384.
14. a) J. T. Singleton, Tetrahedron 2003, 59, 1837;
15. b) J. M. Serrano-Becerra, D. Morales-Morales, Curr. Org. Synth. 2009, 6, 169;
16. c) D. Morales-Morales, Mini-Rev. Org. Chem. 2008, 5, 141;
17. d) D. Benito-Garagorri, K. Kirchner, Ace. Chem. Res. 2008, 41, 201.
18. a) E. Alacid, D. A. Alonso, L. Botella, C. Najera, M. C. Pacheco, Chem. Rec. 2006, 6, 111;
19. b)R.B. Bedford, Chem. Commun. 2003, 15, 1787.
20. N. Phan, M. van der Sluys, C. W. Jones, Adv. Synth. Catal. 2006, 348, 609.
21. I. P. Beletskaya, A. V. Cheprakov, J. Organomet. Chem. 2004, 689, 4055.
22. a) L. Yin, J. Liebscher, Chem. Rev. 2007, 107, 133;
23. b) A. Biffis, Chim. Ind. (Milan, Italy) 2005, 87, 36.
24. a) S. S. Proeckl, W. Kleist, K. Köhler, Inorg. Chem. 2007, 46, 1876;
25. b) W. Kleist, J.-K. Lee, K. Köhler, Eur J Inorg. Chem. 2009, 261;
26. c) K. Koehler, R. G. Heiden-reich, S. S. Soomro, S. S. Proeckl, Adv. Synth. Catal. 2008, 350, 2930.
27. J. M. Richardson, C. W. Jones, J. Catal. 2007, 251, 80.
28. M. Weck, C. W. Jones, Inorg. Chem. 2007, 46, 1865.
29. a) S. Kozuch, S. Shaik, A. Jutand, C. Amatore, Chem. Eur. J. 2004, 10, 3072;
30. b) L. J. Goossen, D. Koley, H. L. Hermann, W. Thiel, Organometallics 2006, 25, 54;
31. c) G. Y. Li, J. Org. Chem. 2002, 67, 3643.
32. A. F. Schmidt, A. Al Halaiqa, V.V. Smirnov, Synlett 2006, 18, 2861.
33. J. G. de Vries, Dalton Trans. 2006, 421.
34. a) D. Astruc, Inorg. Chem. 2007, 46, 1884;
35. b) D. Astruc, F. Lu, J. R. Aranzaes, Angew. Chem. 2005, 117, 8062;
36. Angew. Chem. Int. Ed. 2005, 44, 7852;
37. c) L. Djakovitch, K. Köhler, J. G. de Vries, in: Nanoparticles and Catalysis, (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2008, p303.
38. a) T. Jeffery, M. David, Tetrahedron Lett. 1998, 39, 5751;
39. b) T. Jeffery, Tetrahedron 1996, 52, 10113.
40. For some examples see : a) J. Sakamoto, A. D. Schluter, Eur. J. Org. Chem. 2007, 16, 2700;
41. b) M. Albrecht, R. Froehlich, Synlett 2007, 14, 2295;
42. c) H. Ali, N. Canchou, X E. van Lier, Photochem. Photobiol. Sci. 2009, 8, 868;
43. d) A. Goulomis, G. M. A. Rahman, J. Abel, G. de La Torre, P. Vazquez, L. Echegoyen, D. M. Guldi, T. Torres, Aust. J. Chem. 2008, 61, 256;
44. e) H. Ali, J. E. van Lier, Tetrahedron Lett. 2009, 50, 1113;
45. H. Ali, J. E. van Lier, Tetrahedron Lett. 2009, 50, 337;
46. f) C. A. Barker, X. Zeng, S. Bettington, A. S. Batsanov, M. B. Bryce, A. Becby, Chem. Eur. J. 2007, 13, 6710.
47. I. D. Kostas, A. G. Coutselos, G. Charalambidis, A. Skondra, Tetrahedron Lett. 2007, 48, 6688.
48. Q. Wan, Y. Liu, Catal. Lett. 2009, 128, 487.
49. C. Röhlich, K. Köhler, Chem. Eur. J. 2010, 16, 2363.
50. H. Pilkington, R. Robson, Aust. J. Chem. 1970, 23, 2115.
51. a) B. Dutta, P. Bag, B. Adhikary, U. Flörke, K. Nag, J. Org. Chem. 2004, 69, 5419;
52. b) B. Dutta, B. Adhikary, U. Flörke, K. Nag, Eur. J. Inorg. Chem. 2006, 20, 4111.
53. K. L. Cheng, B. L. Goydish, Microchem. J. 1966, 10, 158.
54. a) S. S. Proeckl, W. Kleist, M. A. Gruber, K. Köhler, Angew. Chem. 2004, 116, 1917;
55. Angew. Chem. Int. Ed. 2004, 43, 1881;
56. S. S. Proeckl, W. Kleist, M. A. Gruber, K. Köhler, Tetrahedron 2005, 61, 9855.
57. a) M. Amirnasr, M. K. Nazeeruddin, M. Gratzel, Thermochim. Acta 2000, 348, 105;
58. b) M. R. R. Prasad, V. N. Krishnamurthy, Thermochim. Acta 1991, 185, 1;
59. c) L. V. Malysheva, E. Paukstis, N. S. Kotsarenko, J. Catal. 1987, 104, 31.
60. A. F. Schmidt, L. V. Mametova, Kinet. Catal. 1996, 37, 406.
61. M. Moreno-Mañas, M. Pérez, R. Pleixats J. Org. Chem. 1996, 61, 2346.
62. W Kleist, S. S. Proeckl, K. Köhler, Catal. Lett. 2008, 125, 197.