Uridate/pyridyl Pd(II) complexes: Phosphine-free high turnover catalysts for the Heck reaction of deactivated aryl bromides

Journal of Organometallic Chemistry

Volumn 696, Issue 3, 2011, Pages 795-801

  Srinivas, Pottabathula ^a   Srinivas, Keesara ^a   Likhar, Pravin R ^a   Sridhar, Balsubramanian ^a   Mohan, Kakita Veera ^a   Bhargava, Suresh ^b   Kantam, Mannepalli Lakshmi ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b RMIT UNIVERSITY   (Australia)

Author keywords

Heck reaction; High turnover; N Ligand; Palladium; Phosphine free

Indexed keywords

ACTIVE CATALYST; ARYL BROMIDES; ARYL CHLORIDE; COORDINATION SITES; HECK REACTIONS; HIGH TURNOVER; N LIGANDS; PALLADIUM COMPLEXES; PHOSPHINE-FREE;

BROMINE COMPOUNDS; CATALYSTS; CHELATION; CHLORINE COMPOUNDS; LIGANDS; METAL HALIDES; PALLADIUM; PHOSPHORUS COMPOUNDS; SYNTHESIS (CHEMICAL);

PALLADIUM COMPOUNDS;

EID: 78751576095     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.09.075     Document Type: Article

References (64)

1. T. Mizoroki, K. Mori, and A. Ozaki Bull. Chem. Soc. Jpn. 44 1971 581
2. R.F. Heck, and J.P. Nolley Jr. J. Org. Chem 37 1972 2320
3. For reviews of the Heck reaction:
4. R.F. Heck Org. React. 27 1982 345
5. A. Spencer J. Organomet. Chem 258 1983 101
6. W. Cabri, and I. Candiani Acc. Chem. Res. 28 1995 2
7. R.F. Heck B.M. Trost, Comprehensive Organic Synthesis 1991 Pergamon New York vol. 4(Chapter 4.3)
8. G.T. Crisp Chem. Soc. Rev. 27 1998 427
9. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009
10. R.F. Heck Acc. Chem. Res. 12 1979 146
11. L.F. Overman, D.J. Ricca, and V.D. Tran J. Am. Chem. Soc. 115 1993 2042
12. K.C. Nicolaou, and E.J. Sorensen Classics in Total Synthesis 1996 VCH New York (Chapter 31)
13. R.A. de Vries, P.C. Vosejpka, and M.L. Ash F.E. Herkes, Catalysis of Organic Reactions 1998 Marcel Dekker New York (Chapter 37)
14. L.F. Tietze, G. Kettschau, U. Heuschert, and G. Nordmann Chem. Eur. J. 7 2001 368
15. Y. Ben-David, M. Portnoy, M. Gozin, and D. Milstein Organometallics 11 1992 1995
16. M. Portnoy, Y. Ben-David, and D. Milstein Organometallics 12 1993 4734
17. A.F. Littke, and G.C. Fu J. Org. Chem 64 1999 10
18. K.H. Shaughnessy, P. Kim, and J.F. Hartwig J. Am. Chem. Soc. 121 1999 2123
19. A. Ehrentraut, A. Zapf, and M. Beller Synlett 2000 1589
20. V.P.W. Bohm, and W.A. Herrmann Chem. Eur. J. 6 2000 1017
21. A.F. Littke, and G.C. Fu J. Am. Chem. Soc. 123 2001 6989
22. V.V. Grushin, and H. Alper Chem. Rev. 94 1994 1047
23. M. Beller, and A. Zapf Synlett 1998 792
24. M.T. Reetz, E. Westermann, R. Lohmer, and G. Lohmer Tetrahedron Lett. 39 1998 8449
25. W.A. Herrmann Angew. Chem. Int. Ed. 41 2002 1290
26. B.S. Yong, and S.P. Nolan Chemtracts: Org. Chem. 2003 205
27. W.A. Herrmann, C. Brossmer, K. Ofele, C.-P. Reisinger, T. Priermeier, M. Beller, and H. Fisher Angew. Chem., Int. Ed. Engl. 34 1995 1844
28. W.A. Herrmann, C. Brossmer, C.-P. Reisinger, T. Priermeier, K. Ofele, and M. Beller Chem. Eur. J. 3 1997 1357
29. X. Gai, R. Grigg, M.I. Ramzan, V. Sridharan, S. Collard, and J.E. Muir Chem. Commun. 2000 2053
30. A.S. Gruber, D.Z. Zim, G. Ebeling, A.L. Monteriro, and J. Dupont Org. Lett. 2 2000 1287
31. S. Gibson, D.F. Foster, G.R. Eastam, R.P. Tooze, and D.J. Cole-Hamilton Chem. Commun. 2001 779
32. C.S. Consorti, M.L. Zanini, S. Leal, G. Ebeling, and J. Dupont Org. Lett. 5 2003 983
33. G.D. Frey, C.-P. Reisinger, E. Herdtweck, and W.A. Herrmann J. Organomet. Chem. 690 2005 3193
34. K.-F. Peng, M.-T. Chen, C.-A. Huang, and C.-T. Chen Eur. J. Inorg. Chem. 2008 2463
35. D. Bourissou, O. Guerret, F.P. Gabbai, and G. Bertrand Chem. Rev. 100 2000 39
36. S.K. Yen, L.L. Koh, F.E. Hahn, H.V. Huynh, and T.S.A. Hor Organometallics 25 2006 5105
37. J. Ye, W. Chen, and D. Wang Dalton Trans. 2008 4015
38. N. Marion, and S.P. Nolan Acc. Chem. Res. 41 2008 1440
39. X. Zhang, Z. Xi, A. Liu, and W. Chen Organometallics 27 2008 4401
40. D. Meyer, M.A. Taige, A. Zeller, K. Hohlfeld, S. Ahrens, and T. Strassner Organometallics 28 2009 2142
41. T. Tu, J. Malineni, X. Bao, and K.H. Dotz Adv. Synth. Catal. 351 2009 1029
42. W.A. Herrmann, K. Ofele, S.K. Schneider, E. Herdtweck, and S.D. Hoffmann Angew. Chem., Int. Ed. 45 2006 3859
43. D.F. Wass, M.F. Haddow, T.W. Hey, A. Guy Orpen, C.A. Russell, R.L. Wingad, and M. Green Chem. Commun. 2007 2704
44. D. Yang, Y.-C. Chen, and N.-Y. Zhu Org. Lett. 6 2004 1577
45. T. Mino, Y. Shirae, Y. Sasai, M. Sakamoto, and T. Fujita J. Org. Chem 71 2006 6834
46. S. Lee J. Organomet. Chem 691 2006 1347
47. X. Cui, Y. Zhou, N. Wang, L. Liu, and Q.-X. Guo Tetrahedron Lett. 48 2007 163
48. X. Cui, J. Li, Z.-P. Zhang, Y. Fu, L. Liu, and Q.-X. Guo J. Org.Chem. 72 2007 9342
49. K. Kawamura, S. Haneda, Z. Gan, K. Eda, and M. Hayashi Organometallics 27 2008 3748
50. F. Li, and T.S.A. Hor Adv. Synth. Catal. 350 2008 2391
51. P. Srinivas, P.R. Likhar, H. Maheswaran, B. Sridhar, K. Ravikumar, and M.L. Kantam Chem. Eur. J. 15 2009 1578
52. M.L. Kantam, P. Srinivas, J. Yadav, P.R. Likhar, and S. Bhargava J. Org. Chem. 74 2009 4882
53. R.A. Gossage, H.A. Jenkins, and P.N. Yadav Tetrahedron Lett. 45 2004 7689
54. V. Montoya, J. Pons, V. Branchadell, J. Garcia-Antón, X. Solans, M. Font-Bardía, and J. Ros Organometallics 27 2008 1084
55. C. Najera, J. Gil-Molto, S. Karlström, and L.R. Falvello Org. Lett. 5 2003 1451
56. G.A. Grasa, A.C. Hillier, and S.P. Nolan Org. Lett. 3 2001 1077
57. V. Farina Adv. Synth. Catal. 346 2004 1553
58. Q. Yao, E.P. Kinney, and Z. Yang J. Org. Chem. 68 2003 7528
59. A.H.M. de Vries, J.M.C.A. Mulders, J.H.M. Mommers, H.J.W. Henderickx, and J.G. de Vries Org. Lett. 5 2003 3285
60. M.T. Reetz, and J.G. de Vries Chem. Commun. 2004 1559
61. See Ref. [7a,b] M.T. Reetz, G. Lohmer, and R. Schwickardi Angew. Chem. Int. Ed. 37 1998 481
62. See Ref. [7d];
63. T. Kawano, T. Shinomaru, and I. Ueda Org. Lett. 4 2002 2545
64. R.B. Bedford, C.S.J. Cazin, and D. Holder Coord. Chem. Rev. 248 2004 2283