Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and application as Suzuki-Miyaura coupling catalysts

Journal of Organometallic Chemistry

Volumn 703, Issue , 2012, Pages 34-42

  Mahamo, Tebello ^a,c   Mogorosi, Mokgolela M ^a   Moss, John R ^a   Mapolie, Selwyn F ^b   Chris Slootweg, J ^c   Lammertsma, Koop ^c   Smith, Gregory S ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

^b STELLENBOSCH UNIVERSITY   (South Africa)

^c VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

Aryl halides; Arylboronic acids; Iminophosphines; Palladium(II) complexes; Suzuki Miyaura coupling

Indexed keywords

ARYL HALIDES; ARYLBORONIC ACIDS; IMINOPHOSPHINES; PALLADIUM(II) COMPLEXES; SUZUKI-MIYAURA COUPLING;

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

PALLADIUM COMPOUNDS;

EID: 84862823845     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2011.12.021     Document Type: Article

References (78)

1. J. Dupont, C.S. Consorti, and J. Spencer Chem. Rev. 105 2005 2527
2. Z. Weng, S. Teo, and T.S.A. Hor Acc. Chem. Rev. 40 2007 676 684
3. J.H. Kirchhoff, M.R. Netherton, I.D. Hills, and G.C. Fu J. Am. Chem. Soc. 124 2002 13662
4. A.A. Bermejo, A. Ros, R. Fernandez, and J.M. Lassaletta J. Am. Chem. Soc. 130 2008 15798
5. G.A. Molander, B.W. Katona, and F. Machruohi J. Org. Chem. 67 2002 8416
6. J.V. Kingston, and J.G. Verkade J. Org. Chem. 72 2007 2816
7. S.D. Dreher, S.-E. Lim, D.L. Sandrock, and G.A. Molander J. Org. Chem. 74 2009 3626
8. G.A. Molander, and C.R. Bernardi J. Org. Chem. 67 2002 8424
9. S. Teo, Z. Weng, and T.S.A. Hor J. Organomet. Chem. 696 2011 2928 2934
10. P. Espinet, and K. Soulantica Coord. Chem. Rev. 193 - 195 1999 499
11. J.C. Jeffrey, and T.B. Rauchfuss Inorg. Chem. 18 1979 2658
12. P. Bhattacharyya, P.B.J. Parr, and A.M. Slawin J.Chem. Soc. Dalton Trans. 1998 3609
13. O.M. Ni Dhubhnhaill, J. Lennon, and M.G.B. Drew Dalton Trans. 2005 3213
14. J.A. Davies, and F.R. Hartley Chem. Rev. 81 1979 2658
15. E. Lindner, M. Haustein, H.A. Mayer, K. Gierling, R. Fawzi, and M. Steinman Organometallics 14 1995 2246
16. T.B. Higgins, and C.A. Mirkin Inorg. Chim. Acta 240 1995 347
17. K.R. Reddy, W.-W. Tsai, K. Surekha, G.-H. Lee, S.-M. Peng, J.-T. Chen, and S.-T. Liu J. Chem. Soc. Dalton, Trans. 2002 1776
18. A.R. Shaffer, and J.A.R. Schmidt Organometallics 27 2008 1259
19. A.R. Shaffer, and A.R. Schmidt Organometallics 28 2009 2494
20. P.J. Guiry, and C.P. Saunders Adv. Synth. Catal. 346 2004 497
21. A.M.Z. Slawin, M.B. Smith, and J.D. Woollins J. Chem. Soc. Dalton Trans. 1996 4575
22. P. Bhattacharyya, A.M.Z. Slawin, M.B. Smith, and J.D. Woollins Inorg. Chem. 35 1996 3675
23. A.M.Z. Slawin, M.B. Smith, and J.D. Woollins J. Chem. Soc. Dalton Trans. 1996 1283
24. A.M.Z. Slawin, M.B. Smith, and J.D. Woollins Polyhedron 15 1996 1579
25. A.I. Polosukhin, O.G. Bondarev, A.V. Korostylev, R. Hilgraf, V.A. Davankov, and K.N. Gavrilov Inorg. Chim. Acta 323 2001 55
26. L. Crociani, G. Bandoli, A. Dolmella, M. Basato, and B. Corain Eur. J. Chem. 1998 1811
27. A. Del Zotto, W. Baratta, M. Ballico, E. Herdtweck, and P. Rigo Organometallics 26 2007 5636
28. E. Shirakawa, Y. Nakao, Y. Murota, and T. Hiyama J. Organomet. Chem. 670 2003 132
29. G.L. Crossetti, C.A. Filgueiras, R.A. Howie, J.L. Wardell, and C.M. Ziglo Acta Cryst. C57 2001 1279
30. O. del Campo, A. Carbayo, J.V. Cuevas, G. Garcia-Herbaso, and A. Munoz Eur. J. Inorg. Chem. 2009 2254
31. H. M- Thibault, B.E.G. Lucier, R.W. Schurko, and F.-G. Fontaine Dalton Trans. 2009 7701
32. C.A. Ghilardi, S. Midollini, S. Moneti, A. Orlandini, and G. Scapacci J. Chem. Soc. Dalton Trans. 1992 3371
33. S.M. Nobre, and A.L. Monteiro J. Mol. Catal. A: Chem. 313 2009 65 73
34. B. Crociani, S. Antonaroli, M. Burattini, F. Benetollo, A. Scrivanti, and M. Bertoldini J. Organomet. Chem. 693 2008 3932
35. A. Scrivianti, M. Bertoldini, U. Matteoli, S. Antonaroli, and B. Crociani Tetrahedron 65 2009 7611
36. B. Crociani, S. Antonaroli, M. Burattini, P. Paoli, and P. Rossi Dalton Trans. 2010 3665
37. A.R. Shaffer, and J.A.R. Schmidt Chem. Eur. J. 15 2009 2662
38. G. Sanchez, J. Garcia, J.L. Serrano, L. Garcia, J. Perez, and G. Lopez Inorg. Chim. Acta 363 2010 1084
39. M.M. Mogorosi, T. Mahamo, J.R. Moss, S.F. Mapolie, J.C. Slootweg, K. Lammertsma, and G.S. Smith J. Organomet. Chem. 696 2011 3585
40. J. Flapper, H. Kooijman, M. Lutz, A.L. Spek, P.W.N.M. van Leeuwen, C.J. Elsevier, and P.C.J. Kamer Organometallics 28 2009 1180
41. H.A. Ankersmit, B.H. Loken, H. Kooijman, A.L. Spek, K. Vrieze, and G. van Koten Inorg. Chim. Acta 252 1996 141
42. P.H.P. Brinkmann, and G.A. Luinstra J. Organomet. Chem. 572 1999 193
43. J.R. Dilworth, S.D. Howe, A.J. Hutson, J.R. Miller, J. Silver, R.M. Thompson, M. Harman, and M.B. Hursthouse J. Chem. Soc. Dalton Trans. 1994 3553
44. P. H- Chen, Y.-H. Liu, S.-M. Peng, and S.-T. Liu Organometallics 22 2003 4893
45. O. Daugulis, and M. Brookhart Organometallics 21 2002 5926
46. B. H-Song, Z. Z-Zhang, and T.C.W. Mak Polyhedron 21 2002 1043
47. P. Bhattacharyya, M.L. Loza, J. Parr, and A.M.Z. Slawin J. Chem. Soc. Dalton Trans. 1999 2917
48. S. Stoccorro, G. Cheluci, A. Zucca, M.A. Cinellu, G. Minghetti, and M. Manassero J. Chem. Soc. Dalton Trans. 1996 1295
49. J.C. Jeffrey, T.B. Rauhfuss, and P.A. Tucker Inorg. Chem. 19 1980 3306
50. P. Crochet, J. Gimeno, J. Borge, and S. Garcia-Granda New J. Chem. 27 2003 414
51. E. Shirakawa, H. Yoshida, and H. Takaya Tetrahedron Lett. 38 1997 3759
52. K.R. Reddy, W.-W. Tsai, K. Surekha, G.-H. Lee, S.-M. Peng, J.-T. Chen, and S.-T. Liu Organometallics 20 2001 1292
53. E.K. van den Beuken, W.J.J. Smeets, A.L. Spek, and B.L. Feringa Chem. Commun. 1998 223
54. A. Alimardanov, L. Schmieder-van de Vondervoort, A.H.M. de Vries, and J.G. de Vries Adv. Synth. Catal. 346 2004 1812
55. A.H.M. de Vries, J. Mulders, J.H.M. Mommers, H.J.W. Henderickx, and J.G. de Vries Org. Lett. 5 2003 3285
56. M.T. Reetz, and J.G. de Vries Chem. Commun. 2004 1559
57. A.V. Gaikwad, A. Holuigue, M.B. Thathagar, J.E. ten Elshof, and G. Rothenberg Chem. Eur. J. 13 2007 6908
58. L.D. Pachon, C.J. Elsevier, and G. Rothenberg Adv. Synth. Catal. 348 2006 1705
59. A.F. Schmidt, and V.V. Smirnov J. Mol. Catal. A: Chem. 203 2003 75
60. Q. Yao, E.P. Kinney, and Z. Yang J. Org. Chem. 68 2003 7528
61. C.M. So, C.C. Yeung, C.P. Lau, and F.Y. Kwong J. Org. Chem. 73 2008 7803
62. R.B. Bedford, S.L. Hazelwood (née Welch), P.N. Horton, and M.B. Hursthouse Dalton Trans. 2003 4164
63. R.B. Bedford, S.L. Hazelwood (née Welch), M.E. Limmert, D.A. Albisson, S.M. Draper, P. Noelle Scully, S.J. Coles, and M.B. Hursthouse Chem. Eur. J. 9 2003 3216
64. D. Olsson, and O.F. Wendt J. Organomet. Chem. 694 2009 3112
65. R. van Asselt, and C.J. Elsevier J. Mol. Catal. 65 1991 L13
66. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
67. G.B. Smith, G.C. Dezeny, D.L. Hughes, A.O. King, and T.R. Verhoeven J. Org. Chem. 59 1994 8151
68. A. Ariafard, Z. Lin, and I.J.S. Fairlamb Organometallics 25 2006 5788
69. A.L. Casado, and P. Espinet J. Am. Chem. Soc. 120 1998 8978
70. P. Espinet, and A.M. Echavarren Angew. Chem. Int. Ed. 43 2004 4704
71. V. Ravindar, H. Hemling, and J. Blum Synth. Commun. 22 1992 1453
72. C.T. Bailey, and G.C. Linsesky J. Chem. Edu. 62 1985 896
73. R.E. Rülke, J.M. Ernsting, A.L. Spek, C.J. Elsevier, P.W.N.M. van Leeuwen, and K. Vrieze Inorg. Chem. 32 1993 5769
74. SAINT Version 7.60a 2006 Bruker AXS Inc Madison, WI, USA
75. G.M. Sheldrick SHELXS-97, SHELXL-97 and SADABS version 2.05 1997 University of Göttingen Germany
76. L.J. Barbour J. Supramol. Chem. 1 2001 189
77. J.L. Atwood, and L.J. Barbour Cryst. Growth Des. 3 2003 3
78. http://www.povray.org.