Seven-membered Pd(II) complexes containing symmetric phosphorus ylides: Synthesis, characterization and high catalytic activity toward Suzuki cross-coupling reactions

Comptes Rendus Chimie

Volumn 17, Issue 1, 2014, Pages 81-90

  Sabounchei, Seyyed Javad ^a   Panahimehr, Mohammad ^a   Ahmadi, Mohsen ^a   Akhlaghi, Fateme ^a   Boscovic, Collete ^b  

^a BU ALI SINA UNIVERSITY   (Iran)

^b UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

Low catalyst loading; Seven membered ring; Suzuki cross coupling reaction; Symmetric phosphorus ylides; X ray crystal structure

Indexed keywords

EID: 84892369353     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2013.05.019     Document Type: Article

References (75)

1. Y. Shen Acc. Chem. Res. 31 1998 584
2. L.R. Falvello, S. Fernandez, R. Navarro, and E.P. Urriolabeitia Inorg. Chem. 39 2000 2957
3. O.I. Kolodiazhnyi Russ. Chem. Rev. 66 1997 225
4. C. Puke, G. Erker, N.C. Aust, E.U. Wurthweine, and R. Frohich J. Am. Chem. Soc. 120 1998 4863
5. S. Kato, T. Kato, M. Mizuta, K. Itoh, and Y. Ishii J. Organomet. Chem. 51 1973 167
6. S.J. Sabounchei, M. Ahmadi, Z. Nasri, E. Shams, S. Salehzadeh, Y. Gholiee, R. Karamian, M. Asadbegy, and S. Samiee C. R. Chimie 16 2013 159
7. M.M. Ebrahim, H. Stoeckli-Evans, and K. Panchanatheswaran Polyhedron 26 2007 3491
8. K. Karami, C. Rizzoli, and F. Borzooie Polyhedron 30 2011 778
9. J. Vicente, M.T. Chicote, J.A. Cayuelas, J. Fernandez-Baeza, P.G. Jones, G.M. Sheldrick, and P. Espinet J. Chem. Soc., Dalton Trans. 6 1985 1163
10. J. Vicente, M.T. Chicote, I. Saura-Llamas, P.G. Jones, K.E. Meyer-B, and C.F. Erdbriigger Organometallics 7 1988 997
11. J. Vicente, M.T. Chicote, I. Saura-Llamas, J. Turpin, and J. Femandez-Baera J. Organomet. Chem. 333 1987 129
12. G. Facchin, L. Zanotto, R. Bertani, L. Canovese, and P. Uguagliati J. Chem. Soc., Dalton Trans. 19 1993 2871
13. G. Facchin, R. Bertani, L. Zanotto, M. Calligaris, and G. Nardin J. Organomet. Chem. 366 1989 409
14. U. Belluco, R.A. Michelin, R. Bertani, G. Facchin, G. Pace, L. Zanotto, M. Mozzon, M. Furlan, and E. Zangrando Inorg. Chim. Acta 252 1996 355
15. U. Belluco, R.A. Michelin, R. Ros, R. Bertani, G. Facchin, M. Mozzon, and L. Zanotto Inorg. Chim. Acta 883 1992 198
16. U. Belluco, R.A. Michelin, M. Mozzon, R. Bertani, G. Facchin, L. Zanotto, and L. Pandolfo J. Organomet. Chem. 557 1998 37
17. A. Spannenberg, W. Baumann, and U. Rosenthal Organometallics 19 2000 3991
18. L.R. Falvello, M.E. Margalejo, R. Navarro, and E.P. Urriolabeitia Inorg. Chim. Acta 347 2003 75
19. F. Benetollo, R. Bertani, P. Ganis, L. Pandolfo, and L. Zanotto J. Organomet. Chem. 629 2001 201
20. S.M. Sbovata, A. Tassan, and G. Facchin Inorg. Chim. Acta 361 2008 3177
21. R.A. Grey, and L.R. Anderson Inorg. Chem. 16 1977 3187
22. N.L. Holy, N.C. Baenziger, and R.M. Flynn Angew. Chem. 90 1978 732
23. K.A.O. Starzewski, and J. Witte Angew. Chem. 100 1988 861
24. R. Uson, A. Laguna, M. Laguna, and I. Lazaro Organometallics 6 1987 2326
25. R. Uson, J. Fornie, R. Navarro, and A.M. Ortega J. Organomet. Chem. 334 1987 389
26. J.B. Ivan, H.C. Shy, C.W. Liu, L.K. Liu, and S.K. Yeh J. Chem. Soc., Dalton Trans. 8 1990 2509
27. H. Schmidbaur, T. Costa, B.M. Mahrla, F.H. Kohler, Y.H. Tsay, C. Kruger, J. Abart, and F.E. Wagner Organometallics 1 1982 1266
28. E. Fluck, K. Bieger, G. Heckmann, and B. Neumuller J. Organomet. Chem. 459 1993 73
29. H. Schmidbaur, C. Paschalidis, O. Steigelmann, and G. Müller Angew. Chem., Int. Ed. 29 1990 516
30. K. Dimroth Acc. Chem. Res. 15 1982 58
31. G. Maerkl, and P. Kreitmeier Comprehensive Heterocyclic Chemistry II 1996 Elsevier Oxford 1019
32. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
33. J. Broggi, H. Clavier, and S.P. Nolan Organometallics 27 2008 5525
34. M.A. Hossain, S. Lucarini, D. Powell, and K. Bowman-James Inorg. Chem. 43 2004 7275
35. T.P. Liu, Y.X. Liao, C.H. Xing, and Q.S. Hu Org. Lett. 13 2011 2452
36. X. Li, F. Yang, and Y. Wu J. Org. Chem. 78 2013 4543
37. I.P. Beletskaya, and A.V. Cheprakov J. Organomet. Chem. 689 2004 4055
38. J. Dupont, C.S. Consorti, and J. Spencer Chem. Rev. 105 2005 2527
39. W.C. Wang, K.F. Peng, M.T. Chen, and C.T. Chen Dalton Trans. 41 2012 3022
40. N. Miyaura, T. Yanagi, and A. Suzuki Synth. Commun. 11 1981 513
41. J.P. Corbet, and G. Mignani Chem. Rev. 106 2006 2651
42. M. Bakherad, A. Keivanloo, A.H. Amin, and S. Jajarmi C. R. Chimie 15 2012 945
43. A. Suzuki Pure Appl. Chem. 57 1985 1749
44. A. Suzuki Pure Appl. Chem. 66 1994 213
45. J. Zhang, L. Zhao, M. Song, T.C.W. Mak, and Y. Wu J. Organomet. Chem. 691 2006 1301
46. S.J. Sabounchei, M. Ahmadi, and Z. Nasri J. Coord. Chem. 66 2013 411
47. S.J. Sabounchei, M. Panahimehr, M. Ahmadi, Z. Nasri, and H.R. Khavasi J. Organomet. Chem. 723 2013 207
48. S.J. Sabounchei, and M. Ahmadi Catal. Comun. 37 2013 114
49. S.J. Sabounchei, and M. Ahmadi Inorg. Chim. Acta 405 2013 15
50. CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysA lis171.NET, compiled Oct 27 2011, 15:02:11).
51. G.M. Sheldrick Acta Crystallogr. A64 2008 112
52. O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard, and H. Puschmann J. Appl. Cryst. 42 2009 339
53. S.J. Sabounchei, H. Nemattalab, S. Salehzadeh, S. Khani, M. Bayat, H. Adams, and M.D. Ward Inorg. Chim. Acta 362 2009 105
54. J. Vicente, M.T. Chicote, M.C. Lagunas, and P.G. Jones J. Chem. Soc., Dalton Trans. 1991 2579
55. S.J. Sabounchei, S. Samiee, D. Nematollahi, A. Naghipour, and D.M. Morales Inorg. Chim. Acta 363 2010 3973
56. S.J. Sabounchei, H. Nemattalab, F. Akhlaghi, and H.R. Khavasi Polyhedron 27 2008 3275
57. S.J. Sabounchei, H. Nemattalab, and H.R. Khavasi X-Ray Struct. Anal. Online 26 2010 35
58. M.M. Ebrahima, K. Panchanatheswaran, A. Neels, and H. Stoeckli-Evans J. Organomet. Chem. 694 2009 643
59. K. Karami, C. Rizzoli, and M. Mohamadi Salah J. Organomet. Chem. 696 2011 940
60. P.R. Kumar, S. Upreti, and A.K. Singh Polyhedron 27 2008 1610
61. J.-H. Li, Q.-M. Zhu, and Y.-X. Xie Tetrahedron 62 2006 10888
62. M.A. Solano-Prado, F. Estudiante-Negrete, and D. Morales-Morales Polyhedron 29 2010 592
63. Z. Zhang, and Z. Wang J. Org. Chem. 71 2006 7485
64. L. Liang, P. Chien, and M. Huang Organometallics 24 2005 353
65. C. Dupuis, K. Adiey, L. Charruault, V. Michelet, M. Savignac, and J. Gene Tetrahedron Lett. 42 2001 6523
66. A.R. Hajipour, K. Karami, and A. Pirisedigh Inorg. Chim. Acta 370 2011 531
67. E. Paetzold, and G. Oehme J. Mol. Catal. A: Chem. 152 2000 69
68. N. Kataoka, Q. Shelby, J.P. Stambuli, and J.F. Hartwig J. Org. Chem. 67 2002 5553
69. V.P.W. Böhm, C.W.K. Gstöttmayr, T. Weskamp, and W.A. Herrmann J. Organomet. Chem. 595 2000 186
70. C. Zhang, and M.L. Trudell Tetrahedron Lett. 41 2000 595
71. A. Fürstner, and A. Leitner Synlett 2 2001 290
72. S.R. ChemLer, D. Trauner, and S.J. Danishefsky Angew. Chem. Int. Ed. 40 2001 4544
73. K. Inamoto, J. Kuroda, K. Hiroya, Y. Noda, M. Watanabe, and T. Sakamoto Organometallics 25 2006 3095
74. J.A. Widegren, and R.G. Finke J. Mol. Catal. A 198 2003 317
75. E. Peris, J.A. Loch, J. Mata, and R.H. Crabtree Chem. Commun. 2 2001 201