Cationic η1/η2-gold(I) complexes of simple arenes

Angewandte Chemie - International Edition

Volumn 45, Issue 33, 2006, Pages 5455-5459

  Herrero Gómez, Elena ^a   Nieto Oberhuber, Cristina ^a   López, Salomé ^a   Benet Buchholz, Jordi ^a   Echavarren, Antonio M ^a  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

interactions; Arene ligands; Enynes; Gold; Phosphanes

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL BONDS; COMPLEXATION; GOLD; SEPARATION;

Π INTERACTIONS; ARENE LIGANDS; ENYNES; PHOSPHANES;

OLEFINS;

EID: 33748659666     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601688     Document Type: Article

References (63)

1. a) S. D. Walker, T. E. Border, J. R. Martinelli, S. L. Buchwald, Angew. Chem. 2004, 116, 1907-1912;
2. Angew. Chem. Int. Ed. 2004, 43, 1871-1876;
3. b) S. Kaye, J. M. Fox, F. A. Hicks, S. L. Buchwald, Adv. Synth. Catal. 2001, 343, 789-794.
4. a) T. E. Barder, J. Am. Chem. Soc. 2006, 128, 898-904;
5. b) U. Christmann, R. Vilar, A. J. P. White, D. J. Williams, Chem. Commun. 2004, 1294-1295;
6. c) U. Christmann, D. A. Pantazis, J. Benet-Buchholz, J. E. McGrady, F. Maseras, R. Vilar, J. Am. Chem. Soc. 2006, 128, 6376-6390.
7. C. Nieto-Oberhuber, S. López, A. M. Echavarren, J. Am. Chem. Soc. 2005, 127, 6178-6179.
8. a) C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460;
9. Angew. Chem. Int.-Ed. 2004, 43, 2402-2406;
10. b) C. Nieto-Oberhuber, M. P. Muñoz, S. López, E. Jiménez-Núñez, C. Nevado, E. Herrero-Gómez, M. Raducan, A. M. Echavarren, Chem. Eur. J. 2006, 12, 1677-1693.
11. a) C. Nieto-Oberhuber, S. López, M. P. Muñoz, D. J. Cárdenas, E. Buñuel, C. Nevado, A. M. Echavarren, Angew. Chem. 2005, 117, 6302-6304;
12. Angew. Chem. Int. Ed. 2005, 44, 6146-6148;
13. b) C. Nieto-Oberhuber, S. López, E. Jiménez- Núñez, A. M. Echavarren, Chem. Eur. J. 2006, 12, 5916-5923.
14. M. P. Muñoz, J. Adrio, J. C. Carretero, A. M. Echavarren, Organometallics 2005, 24, 1293-1300.
15. C. Nieto-Oberhuber, S. López, M. P. Muñoz, E. Jiménez-Núñez, E. Buñuel, D. J. Cárdenas, A. M. Echavarren, Chem. Eur. J. 2006, 12, 1694-1702.
16. Reviews of transition-metal-catalyzed reaction of enynes: a) G. C. Lloyd-Jones, Org. Biomol. Chem. 2003, 1, 215-236;
17. b) C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002, 102, 813-834;
18. c) S. T. Diver, A. Giessert, J. Chem. Rev. 2004, 104, 1317-1382;
19. d) A. M. Echavarren, C. Nevado, Chem. Soc. Rev. 2004, 33, 431-436;
20. e) S. Ma, S. Yu, Z. Gu, Angew. Chem. 2006, 118, 206-209;
21. Angew. Chem. Int. Ed. 2006, 45, 200-203.
22. C. Ferrer, A. M. Echavarren, Angew. Chem. 2006, 118, 1123-1127;
23. Angew. Chem. Int. Ed. 2006, 45, 1105-1109.
24. I complexes: a) F. Gagosz, Org. Lett. 2005, 7, 4129-4132;
25. b) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654-8655;
26. c) L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2004, 126, 11 806-11 807;
27. d) M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10 858-10 859.
28. C. Nevado, A. M. Echavarren, Chem. Eur. J. 2005, 11, 3155-3164.
29. Leading references: a) S. V. Lindeman, R. Rathore, J. K. Kochi, Inorg. Chem. 2000, 39, 5707-5716;
30. b) M. Munakata, L. P. Wu, G. L. Ning, Coord. Chem. Rev. 2000, 198, 171-203;
31. c) M. Munakata, L. P. Wu, T. Kuroda-Sowa, M. Maekawa, Y. Suenaga, G. L. Ning, T. Kojima, J. Am. Chem. Soc. 1998, 120, 8610-8618;
32. d) K. Ogawa, T. Kitagawa, S. Ishida, K. Komatsu, Organometallics 2005, 24, 4842-4844;
33. e) K. K. Laali, S. Hupertz, A. G. Temu, S. E. Galembeck, Org. Biomol. Chem. 2005, 3, 2319-2326;
34. f) R. Rathore, V. J. Chebny, S. H. Abdelwahed, J. Am. Chem. Soc. 2005, 127, 8012-8023.
35. a) F.-B. Xu, Q.-S. Li, L.-Z. Wu, X.-B. Leng, Z.-C. Li, X.-S. Zeng, Y. L. Chow, Z.-Z. Zhang, Organometallics 2003, 22, 633-640;
36. b) Q.-S. Li, C.-Q. Wang, R.-Y. Zou, F.-B. Xu, H.-B. Song, X.-J. Wan, Z.-Z. Zhang, Inorg. Chem. 2006, 45, 1888-1890.
37. 2)] (Tf = trifluoromethanesulfonate) has been reported: N. Mézailles, L. Ricard, F. Gagosz, Org. Lett. 2005, 7, 4133-413; it shows an almost linear arrangement of P-Au-N (174.20(7)°) with a P-Au bond length of 2.2306(7) Å.
38. -.
39. 1 = 0.1013 with negative atomic displacement parameters as a result of correlation effects.
40. -3.
41. -3.
42. -3.
43. -3.
44. N. C. Baenziger, W. E. Bennett, D. M. Soboroff, Acta Crystallogr. Sect. B 1976, 32, 962-963.
45. 3)]: P. Schwerdtfeger, H. L. Hermann, H. Schmidbaur, Inorg. Chem. 2003, 42, 1334-1342.
46. a) F. Bachechi, A. Burini, R. Galassi, B. R. Pietroni, J. Chem. Crystallogr. 2004, 34, 743-748;
47. b) R. C. Bott, P. C. Healy, G. Smitha, Aust. J. Chem. 2004, 57, 213-218;
48. c) K. Nunokawa, S. Onaka, T. Tatematsu, M. Ito, J. Sakai, Inorg. Chim. Acta 2001, 322, 56-64;
49. d) R. C. Bott, G. A. Bowmaker, R. W. Buckley, P. C. Healy, M. C. S. Perera, Aust. J. Chem. 2000, 53, 175-181;
50. e) T. E. Müller, J. C. Green, D. M. P. Mingos, C. M. McPartlin, C. W. D. J. Williams, T. M. Woodroffe, J. Organomet. Chem. 1998, 551, 313-330;
51. f) M. Bardaji, P. G. Jones, A. Laguna, Eur. J. Inorg. Chem. 1998, 989-992;
52. g) K. Angermaier, E. Zeller, H. Schmidbaur, J. Organomet. Chem. 1994, 472, 371-376;
53. h) C. S. W. Harker, E. R. T. Tiekink, Acta Crystallogr. Sect. C 1990, 46, 1546-1547.
54. H. Willner, J. Schaebs, G. Hwang, F. Mistry, R. Jones, J. Trotter, F. Aubke, J. Am. Chem. Soc. 1992, 114, 8972-8980.
55. -3.
56. -3.
57. -3; crystals of this compound break down by cooling to lower temperatures probably as a result of a phase transition.
58. -3.
59. a) A. V. Vasilyev, S. V. Lindeman, J. K. Kochi, Chem. Commun. 2001, 909-910;
60. b) K. Ogawa, T. Kitagawa, S. Ishida, K. Komatsu, Organometallics 2005, 24, 4842-4844.
61. A. L. Balch, M. M. Olmstead, C. Vickery, Inorg. Chem. 1999, 38, 3494-3499.
62. G. M. Sheldrick, SHELXTL Crystallographic System Ver. 5.10, Bruker AXS, Inc., Madison, Wisconsin, 1998.
63. CCDC 605715-605724 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.