Influence of CH3 substituents on tetrahydropyrimidin-2-ylidene: σ-donating properties and in situ catalytic activities of precursor salts/Pd(OAc)2 system for C-C coupling reactions

Journal of Organometallic Chemistry

Volumn 696, Issue 7, 2011, Pages 1359-1366

  Mercan, Deniz ^a   Çetinkaya, Engin ^a   Çetinkaya, Bekir ^a  

^a EGE UNIVERSITY   (Turkey)

Author keywords

Donating ability; C C coupling reactions; N Heterocyclic carbene; Tetrahydropyrimidinium salts

Indexed keywords

C-C COUPLING REACTIONS; CATALYTIC ACTIVITY; IN-SITU; METHYL GROUP; N-HETEROCYCLIC CARBENE; PYRIMIDINE RING; SUZUKI-MIYAURA; TETRAFLUOROBORATES; TETRAHYDROPYRIMIDIN-2-YLIDENE; TETRAHYDROPYRIMIDINIUM SALTS;

CARBON INORGANIC COMPOUNDS; CHEMICAL REACTIONS; FUNCTIONAL GROUPS; RHODIUM COMPOUNDS; SALTS;

CATALYST ACTIVITY;

EID: 79952443279     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.12.041     Document Type: Article

References (62)

1. M. Melaimi, M. Soleilhavoup, and G. Bertrand Angew. Chem. Int. Ed. 49 2010 8810 8849
2. S. Díez-González, N. Marion, and S.P. Nolan Chem. Rev. 109 2009 3612 3676
3. F.E. Hahn, and M.C. Jahnke Angew. Chem. Int. Ed. 47 2008 3122 3172
4. E.A.B. Kantchev, C.J. O'Brien, and M.G. Organ Angew. Chem. Int. Ed. 46 2007 2768 2813
5. S. Díez-González, and S.P. Nolan Coord. Chem. Rev. 251 2007 874 883
6. W.A. Herrmann Angew. Chem. Int. Ed. 41 2002 1290 1309
7. W.A. Herrmann, T. Weskamp, and V.P.W. Bohm Adv. Organomet. Chem. 48 2001 1 69
8. W.A. Herrmann, M. Elison, J. Fischer, C. Köcher, and G.R.J. Artus Angew. Chem. Int. Ed. 34 1995 2371 2374
9. D. Bourissou, O. Guerret, F.P. Gabbaï, and G. Bertrand Chem. Rev. 100 2000 39 91
10. C.M. Crudden, and D.P. Allen Coord. Chem. Rev. 248 2004 2247 2273
11. A.M. Magill, D.S. McGuinness, K.J. Cavell, G.J.P. Britovsek, V.C. Gibson, A.J.P. White, D.J. Williams, A.H. White, and B.W. Skelton J. Organomet. Chem. 617-618 2001 546 560
12. N. Marion, and S.P. Nolan Acc. Chem. Res. 41 2008 1440 1449
13. Y.-X. Jia, D. Katayev, G. Bernardinelli, T.M. Seidel, and E.P. Kündig Chem. Eur. J. 16 2010 6300 6309
14. C.J.E. Davies, M.J. Page, C.E. Ellul, M.F. Mahon, and M.K. Whittlesey Chem. Commun. 46 2010 5151 5153
15. P.D. Newman, K.J. Cavell, and B.M. Kariuki Organometallics 29 2010 2724 2734
16. A. Binobaid, M. Iglesias, D. J Beetstra, B. Kariuki, A. Dervisi, I.A. Fallis, and K.J. Cavell Dalton Trans. 2009 7099 7112
17. C.C. Scarborough, A. Bergant, G.T. Sazama, I.A. Guzei, L.C. Spencer, and S.S. Stahl Tetrahedron 65 2009 5084 5092
18. E.L. Kolychev, I.A. Portnyagin, V.V. Shuntikov, V.N. Khrustalev, and M.S. Nechaev J. Organomet. Chem. 694 2009 2454 2462
19. M. Iglesias, D.J. Beetstra, J.C. Knight, L.-L. Ooi, A. Stasch, S. Coles, L. Male, M.B. Hursthouse, K.J. Cavell, A. Dervisi, and I.A. Fallis Organometallics 27 2008 3279 3289
20. M. Iglesias, D.J. Beetstra, A. Stasch, P.N. Horton, M.B. Hursthouse, S.J. Coles, K.J. Cavell, A. Dervisi, and I.A. Fallis Organometallics 26 2007 4800 4809
21. R. Jazzar, J.-B. Bourg, R.D. Dewhurst, B. Donnadieu, and G. Bertrand J. Org. Chem. 72 2007 3492 3499
22. R. Jazzar, H. Liang, B. Donnadieu, and G. Bertrand J. Organomet. Chem. 691 2006 3201 3205
23. M.M. Rogers, J.E. Wendlandt, I.A. Guzei, and S.S. Stahl Org. Lett. 8 2006 2257 2260
24. B. Bantu, D. Wang, K. Wurst, and M.R. Buchmeiser Tetrahedron 61 2005 12145 12152
25. M. Bortenschlager, M. Mayr, O. Nuyken, and M.R. Buchmeiser J. Mol. Catal. A: Chem. 233 2005 67 71
26. C.C. Scarborough, M.J.W. Grady, I.A. Guzei, B.A. Gandhi, E.E. Bunel, and S.S. Stahl Angew. Chem. Int. Ed. 44 2005 5269 5272
27. N. Imlinger, K. Wurst, and M.R. Buchmeiser Monatsh. Chem. 136 2005 47 57
28. L. Yang, M. Mayr, K. Wurst, and M.R. Buchmeiser Chem. Eur. J. 10 2004 5761 5770
29. M. Mayr, K. Wurst, K.-H. Ongania, and M.R. Buchmeiser Chem. Eur. J. 10 2004 1256 1266
30. W.A. Herrmann, S.K. Schneider, K. Öfele, M. Sakamoto, and E. Herdtweck J. Organomet. Chem. 689 2004 2441 2449
31. S.K. Schneider, W.A. Herrmann, and E. Herdtweck J. Mol. Catal. A: Chem. 245 2006 248 254
32. S. Yaar, E.Ö. Özcan, N. Gürbüz, B. etinkaya, and I. Özdemir Molecules 15 2010 649 659
33. I. Özdemir, S. Demir, and B. etinkaya Tetrahedron 61 2005 9791 9798
34. L. Benhamou, N. Vujkovic, V. César, H. Gornitzka, N. Lugan, and G. Lavigne Organometallics 29 2010 2616 2630
35. D. Mendoza-Espinosa, B. Donnadieu, and G. Bertrand J. Am. Chem. Soc. 132 2010 7264 7265
36. K.M. Kuhn, J.-B. Bourg, C.K. Chung, S.C. Virgil, and R.H. Grubbs J. Am. Chem. Soc. 131 2009 5313 5320
37. S. Gaillard, X. Bantreil, A.M.Z. Slawin, and S.P. Nolan Dalton Trans. 2009 6967 6971
38. S. Urban, M. Tursky, R. Fröhlich, and F. Glorius Dalton Trans. 2009 6934 6940
39. S. Würtz, and F. Glorius Acc. Chem. Res. 41 2008 1523 1533
40. A. Bittermann, P. Härter, E. Herdtweck, S.D. Hoffmann, and W.A. Herrmann J. Organomet. Chem. 693 2008 2079 2090
41. J. Yun, E.R. Marinez, and R.H. Grubbs Organometallics 23 2004 4172 4173
42. R.S. Holdroyd, M.J. Page, M.R. Warren, and M.K. Whittlesey Tetrahedron Lett. 51 2010 557 559
43. R. Armstrong, C. Ecott, E. Mas-Marzá, M.J. Page, M.F. Mahon, and M.K. Whittlesey Organometallics 29 2010 991 997
44. G.C. Lloyd-Jones, R.W. Alder, and G.J.J. Owen-Smith Chem. Eur. J. 12 2006 5361 5375
45. R.W. Alder, M.E. Blake, L. Chaker, J.N. Harvey, F. Paolini, and J. Schütz Angew. Chem. Int. Ed. 43 2004 5896 5911
46. F.E. Hahn, L. Wittenbecher, D. Le Van, and R. Fröhlich Angew. Chem. Int. Ed. 39 2000 No. 3
47. M.K. Denk, K. Hatano, and M. Ma Tetrahedron Lett. 40 1999 2057 2060
48. M.K. Denk, A. Thadani, K. Hatano, and A.J. Lough Angew. Chem. Int. Ed. 36 1997 2607 2609
49. E. etinkaya, P.B. Hitchcock, H.A. Jasim, M.F. Lappert, and K. Spyropoulos J. Chem. Soc. Perkin Trans. 1 1992
50. S. Wolf, and H. Plenio J. Organomet. Chem. 694 2009 1487 1492
51. H. Türkmen, O. Sahin, O. Büyükgüngör, and B. etinkaya Eur. J. Inorg. Chem. 2006 4915 4921
52. K. Denk, P. Sirsch, and W.A. Herrmann J. Organomet. Chem. 649 2002 219 224
53. M. Iglesias, D.J. Beetstra, B. Kariuki, K.J. Cavell, A. Dervisi, and I.A. Fallis Eur. J. Inorg. Chem. 2009 1913 1919
54. V. César, N. Lugan, and G. Lavigne Eur. J. Inorg. Chem. 2010 361 365
55. U. Siemeling, C. Färber, M. Leibold, C. Bruhn, P. Mücke, R.F. Winter, B. Sarkar, M. von Hopffgarten, and G. Frenking Eur. J. Inorg. Chem. 2009 4607 4612
56. U. Siemeling, C. Färber, and C. Bruhn Chem. Commun. 2009 98 100
57. D.M. Khramov, E.L. Rosen, V.M. Lynch, and C.W. Bielawski Angew. Chem. Int. Ed. 47 2008 2267 2270
58. T.W. Hudnall, and C.W. Bielawski J. Am. Chem. Soc. 131 2009 16039 16041
59. D.G. Gusev Organometallics 28 2009 763 770
60. V. César, N. Lugan, and G. Lavigne J. Am. Chem. Soc. 130 2008 11286 11287
61. I. Özdemir, S. Demir, B. etinkaya, and E. etinkaya J. Organomet. Chem. 690 2005 5849 5855
62. M. Ulusoy, E. etinkaya, and B. etinkaya Appl. Organomet. Chem. 23 2009 68 74