Facile transmetalation of a pyridyl-phosphine ligand from ruthenium to gold and silver

Journal of Organometallic Chemistry

Volumn 727, Issue , 2013, Pages 1-9

  Tomás Mendivil, Eder ^a   García Álvarez, Rocío ^a   García Garrido, Sergio E ^a   Díez, Josefina ^a   Crochet, Pascale ^a   Cadierno, Victorio ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Dimethyl sulfide; Gold complexes; P,N ligands; Silver complexes; Transmetalation processes

Indexed keywords

DIMETHYL SULFIDE; GOLD COMPLEXES; N-LIGANDS; SILVER COMPLEXES; TRANSMETALATION;

DICHLOROMETHANE; GOLD; GOLD COMPOUNDS; LIGANDS; PHOSPHORUS COMPOUNDS; PROTONATION; RUTHENIUM COMPOUNDS; SILVER COMPOUNDS; X RAY DIFFRACTION;

SILVER;

EID: 84873650551     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2012.12.027     Document Type: Article

References (103)

1. G.R. Newkome Chem. Rev. 93 1993 2067 2089
2. Z.-Z. Zhang, and H. Cheng Coord. Chem. Rev. 147 1996 1 39
3. P. Espinet, and K. Soulantica Coord. Chem. Rev. 193-195 1999 499 556
4. A.P. Sadimenko Adv. Heterocycl. Chem. 104 2011 391 475
5. A. Bader, and E. Lindner Coord. Chem. Rev. 108 1991 27 110
6. C.S. Slone, D.A. Weinberger, and C.A. Mirkin Prog. Inorg. Chem. 48 1999 233 250
7. P. Braunstein, and F. Naud Angew. Chem. Int. Ed. 40 2001 680 699
8. M. Bassetti Eur. J. Inorg. Chem. 2006 4473 4482
9. D.B. Grotjahn Chem. Eur. J. 11 2005 7146 7153
10. A.S. Borovik Acc. Chem. Res. 38 2005 54 61
11. T. Ikariya, K. Murata, and R. Noyori Org. Biomol. Chem. 4 2006 393 406
12. T. Ikariya, and A.J. Blacker Acc. Chem. Res. 40 2007 1300 1308
13. D.B. Grotjahn Dalton Trans. 2008 6497 6508
14. D. Natale, and J.C. Mareque-Rivas Chem. Commun. 2008 425 437
15. D.H. Paull, C.J. Abraham, M.T. Scerba, E. Alden-Danforth, and T. Lectka Acc. Chem. Res. 41 2008 655 663
16. D.B. Grotjahn Chem. Lett. 39 2010 908 914
17. D.B. Grotjahn Pure Appl. Chem. 82 2010 635 647
18. T. Ikariya, and I.D. Gridnev Top. Catal. 53 2010 894 901
19. D.B. Grotjahn Top. Catal. 53 2010 1009 1014
20. D.B. Grotjahn, C.D. Incarvito, and A.L. Rheingold Angew. Chem. Int. Ed. 40 2001 3884 3887
21. D.B. Grotjahn, and D.A. Lev J. Am. Chem. Soc. 126 2004 12232 12233
22. T. Oshiki, H. Yamashita, K. Sawada, M. Utsunomiya, K. Takahashi, and K. Takai Organometallics 24 2005 6287 6290
23. T. Oshiki, I. Hyodo, and A. Ishizuka J. Synth. Org. Chem. Jpn. 68 2010 41 51
24. M. Muranaka, I. Hyodo, W. Okumura, and T. Oshiki Catal. Today 164 2011 552 555
25. V. Cadierno, J. Francos, and J. Gimeno Chem. Eur. J. 14 2008 6601 6605
26. R. García-Álvarez, J. Díez, P. Crochet, and V. Cadierno Organometallics 29 2010 3955 3965
27. V. Cadierno, J. Díez, J. Francos, and J. Gimeno Chem. Eur. J. 16 2010 9808 9817
28. S.E. García-Garrido, J. Francos, V. Cadierno, J.-M. Basset, and V. Polshettiwar ChemSusChem 4 2011 104 111
29. R. García-Álvarez, J. Francos, P. Crochet, and V. Cadierno Tetrahedron Lett. 52 2011 4218 4220
30. R. García-Álvarez, J. Díez, P. Crochet, and V. Cadierno Organometallics 30 2011 5442 5451
31. R. García-Álvarez, A.E. Díaz-Álvarez, J. Borge, P. Crochet, and V. Cadierno Organometallics 31 2012 6482 6490
32. R. García-Álvarez, S.E. García-Garrido, J. Díez, P. Crochet, and V. Cadierno Eur. J. Inorg. Chem. 2012 4218 4230
33. T. Kribber, A. Labonne, and L. Hintermann Synthesis 2007 2809 2818
34. A. Labonne, L. Zani, L. Hintermann, and C. Bolm J. Org. Chem. 72 2007 5704 5708
35. L. Hintermann, L. Xiao, and A. Labonne Angew. Chem. Int. Ed. 47 2008 8246 8250
36. L. Hintermann, T.T. Dang, A. Labonne, T. Kribber, L. Xiao, and P. Naumov Chem. Eur. J. 15 2009 7167 7179
37. F. Boeck, T. Kribber, L. Xiao, and L. Hintermann J. Am. Chem. Soc. 133 2011 8138 8141
38. I. Angurell, O. Rossell, M. Seco, and E. Ruiz Organometallics 24 2005 6365 6373
39. I. Angurell, O. Rossell, and M. Seco Chem. Eur. J. 15 2009 2932 2940
40. M.A. Bennett, T.-N. Huang, T.W. Matheson, and A.K. Smith Inorg. Synth. 21 1982 74 78
41. L. Porri, M.C. Gallazzi, A. Colombo, and G. Allegra Tetrahedron Lett. 47 1965 4187 4189
42. A. Salzer, A. Bauer, S. Geyser, F. Podewils, G.C. Turpin, and R.D. Ernst Inorg. Synth. 34 2004 59 65
43. M.-C. Brandys, M.C. Jennings, and R.J. Puddephatt J. Chem. Soc. Dalton Trans. 2000 4601 4606
44. M. Gaye, B. Demerseman, and P.H. Dixneuf J. Organomet. Chem. 411 1991 263 270
45. E. Hodson, and S.J. Simpson Polyhedron 23 2004 2695 2707
46. CrysAlisPro CCD & CrysAlisPro RED 2008 Oxford Diffraction Ltd. Oxford, UK
47. L.J. Farrugia J. Appl. Cryst 32 1999 837 838
48. M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G.L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, and R. Spagna J. Appl. Cryst. 38 2005 381 388
49. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M.C. Burla, G. Polidori, and M. Camalli J. Appl. Cryst. 27 1994 435 436
50. P.T. Beurskens, G. Admiraal, G. Beurskens, W.P. Bosman, S. García-Granda, R.O. Gould, J.M.M. Smits, and C. Smykalla The DIRDIF Program System Technical report of the Crystallographic Laboratory 1999 University of Nijmegen Nijmegen, The Netherlands
51. G.M. Sheldrick SHELXL97: Program for the Refinement of Crystal Structures 1997 University of Göttingen Göttingen, Germany
52. M. Nardelli Comput. Chem. 7 1983 95 98
53. L.J. Farrugia J. Appl. Cryst. 30 1997 565
54. P. Pyykkö Chem. Rev. 97 1997 597 636
55. H. Schmidbaur Gold Bull. 33 2000 3 10
56. M. Bardají, and A. Laguna Eur. J. Inorg. Chem. 2003 3069 3079
57. C.-M. Che, and S.-W. Lai Coord. Chem. Rev. 249 2005 1296 1309
58. D.L. Phillips, C.-M. Che, K.H. Leung, Z. Mao, and M.-C. Tse Coord. Chem. Rev. 249 2005 1476 1490
59. N.W. Alcock, P. Moore, P.A. Lampe, and K.F. Mok J. Chem. Soc. Dalton Trans. 1982 207 210
60. M. Crespo Organometallics 31 2012 1216 1234
61. S.M. Nabavizadeh, H. Amini, H.R. Shahsavari, M. Namdar, M. Rashidi, R. Kia, B. Hemmateenejad, M. Nekoeinia, A. Ariafard, F.N. Hosseini, A. Gharavi, A. Khalafi-Nezhad, M.T. Sharbati, and F. Panahi Organometallics 30 2011 1466 1477
62. G. Sánchez, J. García, M. Martínez, A.R. Kapdi, J. Pérez, L. García, and J.L. Serrano Dalton Trans. 40 2011 12676 12689
63. S.M. Nabavizadeh, H.R. Shahsavari, M. Namdar, and M. Rashidi J. Organomet. Chem. 696 2011 3564 3571
64. H.F. Liu, W. Liu, P. Zhang, M.S. Huang, and L.X. Zhen J. Xiamen Univ. (Nat. Sci.) 31 1992 57 60
65. M.E. Olmos, A. Schier, and H. Schmidbaur Z. Naturforsch. B 52 1997 203 208
66. A. Del Zotto, and E. Zangrando Inorg. Chim. Acta 277 1998 111 117
67. A. Cingolani, D. Martini, C. Pettinari, B.W. Skelton, and A.H. White Inorg. Chim. Acta 359 2006 2183 2193
68. O. Crespo, M.C. Gimeno, A. Laguna, and C. Larraz Z. Naturforsch. B 64 2009 1525 1534
69. M. Jansen Angew. Chem. Int. Ed. 26 1987 1098 1110
70. A. Caballero, F.A. Jalón, and B.R. Manzano Chem. Commun. 1998 1879 1880
71. L. Hirsivaara, M. Haukka, and J. Pursiainen Inorg. Chem. Commun. 3 2000 508 510
72. L. Hao, M.A. Mansour, R.J. Lachicotte, H.J. Gysling, and R. Eisenberg Inorg. Chem. 39 2000 5520 5529
73. A. Caballero, F.A. Jalón, B.R. Manzano, G. Espino, M. Pérez-Manrique, A. Mucientes, F.J. Poblete, and M. Maestro Organometallics 23 2004 5694 5706
74. F.A. Jalón, B.R. Manzano, A. Caballero, M.C. Carrión, L. Santos, G. Espino, and M. Moreno J. Am. Chem. Soc. 127 2005 15364 15365
75. P. Li, M. Wang, L. Chen, J. Liu, Z. Zhao, and L. Sun Dalton Trans. 2009 1919 1926
76. J. Liu, C. Jacob, K.J. Sheridan, F. Al-Mosule, B.T. Heaton, J.A. Iggo, M. Matthews, J. Pelletier, R. Whyman, J.F. Bickley, and A. Steiner Dalton Trans. 39 2010 7921 7935
77. 6 salt in non-coordinating solvents have been previously described: R. Fernández-Galán, B.R. Manzano, A. Otero, M. Lanfranchi, and M.A. Pellinghelli Inorg. Chem. 33 1994 2309 2312
78. V. Cadierno, P. Crochet, J. Díez, J. García-Álvarez, S.E. García-Garrido, J. Gimeno, S. García-Granda, and M.A. Rodríguez Inorg. Chem. 42 2003 3293 3307
79. A.M.Z. Slawin, J. Wheatley, M.V. Wheatley, and J.D. Woollins Polyhedron 22 2003 1397 1405
80. V. Cadierno, P. Crochet, J. Díez, J. García-Álvarez, S.E. García-Garrido, S. García-Granda, J. Gimeno, and M.A. Rodríguez Dalton Trans. 2003 3240 3249
81. H.L. Milton, M.V. Wheatley, A.M.Z. Slawin, and J.D. Woollins Inorg. Chim. Acta 358 2005 1393 1400
82. S.Y. Ng, G.K. Tan, L.L. Koh, W.K. Leong, and L.Y. Goh Organometallics 26 2007 3352 3361
83. C. Xu, S.A. Pullarkat, and L.Y. Goh Aust. J. Chem. 62 2009 1537 1543
84. R.K. Gupta, A.K. Singh, M. Yadav, P. Kumar, S.K. Singh, P. Li, Q. Xu, and D.S. Pandey J. Organomet. Chem. 695 2010 1924 1931
85. J. Díez, J. Gimeno, I. Merino, E. Rubio, and F.J. Suárez Inorg. Chem. 50 2011 4868 4881
86. L. Bellarosa, J. Díez, J. Gimeno, A. Lledós, F.J. Suárez, G. Ujaque, and C. Vicent Chem. Eur. J. 18 2012 7749 7765
87. J. Díez, J. Gimeno, A. Lledós, F.J. Suárez, and C. Vicent ACS Catal. 2 2012 2087 2099
88. Metal-bound chlorine atoms are well-known hydrogen-bond acceptors: G. Aullón, D. Bellamy, L. Brammer, E.A. Bruton, and A.G. Orpen Chem. Commun. 1998 653 654
89. G.A. Jeffrey An Introduction to Hydrogen Bonding 1997 Oxford University Press Oxford
90. T. Steiner Angew. Chem. Int. Ed. 41 2002 48 76
91. R.A. Head, J.F. Nixon, J.R. Swain, and C.M. Woodard J. Organomet. Chem. 76 1974 393 400
92. D.N. Cox, R.W.H. Small, and R. Roulet J. Chem. Soc. Dalton Trans. 1991 2013 2018
93. J.G. Toerien, and P.H. van Rooyen J. Chem. Soc. Dalton Trans. 1991 2693 2702
94. S. Wache, W.A. Herrmann, G. Artus, O. Nuyken, and D. Wolf J. Organomet. Chem. 491 1995 181 188
95. H. Werner, G. Fries, and B. Weberndörfer J. Organomet. Chem. 607 2000 182 193
96. V. Cadierno, S.E. García-Garrido, and J. Gimeno J. Organomet. Chem. 637-639 2001 767 771
97. Q. Zhang, S.M. Aucott, A.M.Z. Slawin, and J.D. Woollins Eur. J. Inorg. Chem. 2002 1635 1646
98. V. Cadierno, J. Díez, S.E. García-Garrido, S. García-Granda, and J. Gimeno J. Chem. Soc. Dalton Trans. 2002 1465 1472
99. H. Werner, W. Stüer, S. Jung, B. Weberndörfer, and J. Wolf Eur. J. Inorg. Chem. 2002 1076 1080
100. V. Cadierno, S.E. García-Garrido, and J. Gimeno Inorg. Chim. Acta 347 2003 41 48
101. Q. Zhang, G. Hua, P. Bhattacharyya, A.M.Z. Slawin, and J.D. Woollins Dalton Trans. 2003 3250 3257
102. V. Cadierno, S.E. García-Garrido, J. Gimeno, A. Varela-Álvarez, and J.A. Sordo J. Am. Chem. Soc. 128 2006 1360 1370
103. V. Cadierno, J. Francos, and J. Gimeno Organometallics 30 2011 852 862