A lutidine-bridged bis-perimidinium salt: Synthesis and application as a precursor in palladium-catalyzed cross-coupling reactions

Advanced Synthesis and Catalysis

Volumn 351, Issue 7-8, 2009, Pages 1029-1034

  Tu, Tao ^a   Malineni, Jagadeesh ^a   Bao, Xiaoling ^a   Dötz, Karl Heinz ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Carbenes; Heck reaction; Palladium; Perimidinium salts; Suzuki coupling

Indexed keywords

EID: 66149101565     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800768     Document Type: Article

References (52)

1. a) J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527;
2. b) M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759;
3. c) M. Albrecht, G. van Ko-ten, Angew. Chem. 2001, 113, 3866;
4. Angew. Chem. Int. Ed. 2001, 40, 3750.
5. a) F. E. Hahn, M. C. Jahnke, Angew. Chem. 2008, 120, 3166;
6. Angew. Chem. Int. Ed. 2008, 47, 3122;
7. b) Recent developments in the organometallic chemistry of N-het-erocyclic carbenes, (Ed.: R. H. Crab tree), Coord. Chem. Rev. 2007, 251, 595-896;
8. c) N-Heterocyclic Carbenes in Transition Metal Catalysis, (Ed.: F. Glorius), Top. Organomet. Chem. 2007, 21, 1-218;
9. d) O. Kuehl, Chem. Soc. Rev. 2007, 36, 592;
10. e) A. J. Boydston, C. W. Bielawski, Dalton Trans. 2006, 4073;
11. f) F. E. Hahn, Angew. Chem. 2006, 118, 1374;
12. Angew Chem. Int. Ed. 2006, 45, 1348;
13. g) S. P. Nolan, N-Heterocyclic Carbenes in Synthesis, Wiley-VCH, Weinheim, 2006,
14. a) N. Marion, S. P. Nolan, Acc. Chem. Res. 2008, 41, 1440;
15. b) N Marion, S. P. Nolan, Chem. Soc. Rev. 2008, 37, 1776;
16. c) S. Wuertz, F. Glorius, Acc. Chem. Res. 2008, 41, 1523;
17. d) N Marion, S. Diez-Gonzalez, S. P. Nolan, Angew. Chem. 2007, 119, 3046;
18. Angew. Chem. Int. Ed. 2007, 46, 2988.
19. a) P. Bazinet, T.-G. Ong, J. S. O'Brien, N. Lavoie, E. Bell, G. P. A. Yap, I. Korobkov, D. S. Richeson, Organometallics 2007, 26, 2885;
20. b) Ö. Alýcý, N. Gürbüz, B. Çetinkaya, Russ. J. Coord. Chem. 2005, 31, 142;
21. c) İ. Özdemir, B. Alici, N. Gürbüz, E. Çetinkaya, B. Çetinkaya, J. Mol. Catal. A: Chem. 2004, 217, 37;
22. d) P. Bazinet, G. P. A. Yap, D. S. Richeson, J. Am. Chem. Soc. 2003, 125, 13314.
23. a) D. Benito-Garagorri, K. Kirchner, Acc. Chem. Res. 2008, 41, 201;
24. b) D. Pugh, A. A. Danopoulos, Coord. Chem. Rev. 2007, 251, 610;
25. c) E. Peris, R. H. Crabtree, Coord. Chem. Rev. 2007, 248, 2239;
26. d) P. A. Chase, M. Lutz, A. L. Spek, G. P. M. van Klink, G. van Koten, J. Mol. Catal. A: Chem. 2006, 254, 2,
27. a) A. V. Zabula, T. Pape, A. Hepp, F. M. Schappacher, U. C. Rodewald, R. Poettgen, E. F. Hahn, J. Am. Chem. Soc. 2008, 130, 5648;
28. b) F. E. Hahn, M. C. Jahnke, T. Pape, Organometallics 2007, 26, 150;
29. c) F. E. Hahn, M. C. Jahnke, T. Pape, Organometallics 2006, 25, 5927;
30. d) F. E. Hahn, M. C. Jahnke, V. Gomez-Benitez, D. Morales-Morales, T. Pape, Organometallics 2005, 24, 6458.
31. a) T. Tu, X. Bao, W. Assenmacher, H. Peterlik, J. Daniels, K. H. Dotz, Chem. Eur. J. 2009, 25, 1853;
32. b) T. Tu, W. Assenmacher, H. Peterlik, R. Weisbarth, M. Nieger, K. H. Dotz, Angew. Chem. 2007, 119, 6486;
33. Angew. Chem. Int. Ed. 2007, 46, 6368.
34. T. Tu, J. Malineni, K. H. Dotz, Adv. Synth. Catal. 2008, 350, 1791.
35. T. Tu, W. Assenmacher, H. Peterlik, G. Schnakenburg, K. H. Dotz, Angew. Chem. 2008, 120, 7236;
36. Angew. Chem. Int. Ed. 2008, 47, 7127.
37. a) B. Alici, I. Ozdemir, K. Karaaslan, E. Cetinkaya, B. Cetinkaya, J. Mol. Catal. A: Chem. 2005, 231, 261;
38. b) B. Alici, T. Hokelek, E. Cetinkaya, B. Cetinkaya, Hetero-at. Chem. 2003, 14, 82.
39. a) T. Klawonn, A. Gansauer, I. Winkler, T. Lauterbach, D. Franke, R. J. M. Nolte, M. C. Feiters, H. Borner, J. Hentschel, K. H. Dotz, Chem. Commun. 2007, 1894;
40. b) G. Biihler, M. C. Feiters, R. J. M. Nolte, K. H. Dotz, Angew. Chem. 2003, 115, 2599;
41. Angew. Chem. Int. Ed. 2003, 42, 2494.
42. a) N. T. S. Phan, M. Van Der Sluys, C. W. Jones, Adv. Synth. Catal. 2006, 348, 609;
43. b) K. Q. Yu, W. Sommer, J. M. Richardson, M. Week, C. W. Jones, Adv. Synth. Catal. 2005, 347, 161;
44. c) K. Q. Yu, W. Sommer, M. Week, C. W Jones, J. Catal. 2004, 226, 101;
45. d) W J. Sommer, K. Q. Yu, J. S. Sears, Y. Y. Ji, X. L. Zheng, R. J. Davis, C. D. Sherrill, C. W Jones, M. Week, Organometallics 2005, 24, 4351.
46. D. E. Bergbreiter, P. L. Osbum, J. D. Frels, Adv. Synth. Catal. 2005, 347, 172.
47. a) D. Olsson, P. Nilsson, M. El Masnaouy, O. F. Wendt, Dalton Trans. 2005, 1924;
48. b) P. Nilsson, O. F. Wendt, J. Organomet. Chem. 2005, 690, 4197;
49. c) M. R. Eberhard, Org. Lett. 2004, 6, 2125.
50. a) E. Peris, R. H. Crabtree, Coord. Chem. Rev. 2004, 248, 2239;
51. b) E. Peris, J. A. Loch, J. Mata, R. H. Crab-tree, Chem. Commun. 2001, 201.
52. R. S. Simons, P. Custer, C. A. Tessier, W. J. Youngs, Organometallics 2003, 22, 1979.