Gold compounds anchored to a metalated arene scaffold: Synthesis, X-ray molecular structures, and cycloisomerization of enyne

Organometallics

Volumn 32, Issue 6, 2013, Pages 1665-1673

  Dubarle Offner, Julien ^a   Barbazanges, Marion ^a   Augé, Myleìne ^a   Desmarets, Christophe ^a   Moussa, Jamal ^a   Axet, M Rosa ^a   Ollivier, Cyril ^a   Aubert, Corinne ^a   Fensterbank, Louis ^a   Gandon, Vincent ^a,b,c   Malacria, Max ^a   Gontard, Geoffrey ^a   Amouri, Hani ^a  

^a SORBONNE UNIVERSITÉ   (France)

^b UNIVERSITÉ PARIS SACLAY   (France)

^c INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COMPARATIVE STUDIES; CYCLOISOMERIZATION REACTIONS; CYCLOISOMERIZATIONS; ELECTRONIC NATURES; ELECTRONWITHDRAWING; SINGLE CRYSTAL X-RAY DIFFRACTION; TRIFLUOROMETHYL GROUP; X-RAY MOLECULAR STRUCTURE;

FUNCTIONAL GROUPS; GOLD; GOLD COMPOUNDS; ISOMERIZATION; LIGANDS; MOLECULAR STRUCTURE; ORGANOMETALLICS; RUTHENIUM; X RAY DIFFRACTION;

SCAFFOLDS;

EID: 84875411948     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om301101z     Document Type: Article

References (77)

1. Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications; Dai, L.-X., Hou, X.-L., Eds.; Wiley-VCH: Weinheim, Germany, 2010.
2. Ferrocenes. Ligands, Materials and Biomolecules; Stepnicka, P., Ed.; Wiley: Sussex, England, 2008.
3. Das, M. C.; Xiang, S.; Zhang, Z.; Chen, B. Angew. Chem., Int. Ed. 2011, 50, 10510
4. Ferrocenes. Homogenous Catalysis, Organic Synthesis/Material Science; Togni, A.; Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995.
5. Barreiro, E. M.; Broggini, D. F. D.; Adrio, L. A.; White, A. J. P.; Schwenk, R.; Togni, A.; Hii, K. K. Organometallics 2012, 31, 3745
6. Rupnicki, L.; Saxena, A.; Lam, H. W. J. Am. Chem. Soc. 2009, 131, 10386
7. Arrayas, R. G.; Adrio, J.; Carretero, J. C. Angew. Chem., Int. Ed. 2006, 45, 7674 and references therein
8. Singh, N.; Elias, A. J. Organometallics 2012, 31, 2059
9. Carmichael, D.; Klankermayer, J.; Muller, E.; Pietrusiewicz, K. M.; Ricard, L.; Seeboth, N.; Sowa, S.; Stankevic, M. Organometallics 2011, 30, 1804
10. Buchgraber, P.; Mercier, A.; Yeo, W. C.; Besnard, C.; Kundig, E. P. Organometallics 2011, 30, 6303
11. Fowler, K. G.; Littlefield, S. L.; Baird, M. C.; Budzelaar, P. H. M. Organometallics 2011, 30, 6098
12. Wechsler, D.; Rankin, M. A.; McDonald, R.; Ferguson, M. J.; Schatte, G.; Stradiotto, M. Organometallics 2007, 26, 6418
13. Caldwell, H.; Isseponi, S.; Pregosin, P. S.; Albinati, A.; Rizzato, S. J. Organomet. Chem. 2007, 692, 4043
14. Aneetha, H.; Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P. Organometallics 2002, 21, 5334
15. Amouri, H.; Moussa, J.; Renfrew, A. K.; Dyson, P. J.; Rager, M. N.; Chamoreau, L.-M. Angew. Chem., Int. Ed. 2010, 49, 7530
16. Moussa, J.; Rager, M. N.; Boubekeur, K.; Amouri, H. Eur. J. Inorg. Chem. 2007, 2648
17. Moussa, J.; Lev, D. A.; Boubekeur, K.; Rager, M. N.; Amouri, H. Angew. Chem., Int. Ed. 2006, 45, 3854
18. Moussa, J.; Guyard-Duhayon, C.; Herson, P.; Amouri, H.; Rager, M. N.; Jutand, A. Organometallics 2004, 23, 6231
19. Amouri, H.; Thouvenot, R.; Gruselle, M. C. R. Chim. 2002, 5, 257
20. Le Bras, J.; Amouri, H.; Vaissermann, J. Organometallics 1998, 17, 1116
21. Damas, A.; Moussa, J.; Rager, M. N.; Amouri, H. Chirality 2010, 22, 889
22. Moussa, J.; Rager, M. N.; Chamoreau, L.-M.; Ricard, L.; Amouri, H. Organometallics 2009, 28, 397
23. Moussa, J.; Amouri, H. Angew. Chem., Int. Ed. 2008, 47, 1372
24. Moussa, J.; Guyard-Duhayon, C.; Boubekeur, K.; Amouri, H.; Yip, S. K.; Yam, V. W. W. Cryst. Growth Des. 2007, 7, 962
25. Moussa, J.; Wong, K.; M.-C.; Chamoreau, L.-M.; Amouri, H.; Yam, V. W.-W. Dalton Trans. 2007, 3526
26. Axet, M. R.; Barbazanges, M.; Augé, M.; Desmarets, C.; Moussa, J.; Ollivier, C.; Aubert, C.; Fensterbank, L.; Gandon, V.; Malacria, M.; Chamoreau, L.-M.; Amouri, H. Organometallics 2010, 29, 6636
27. Shapiro, N. D.; Toste, F. D. Synlett 2010, 5, 675
28. Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208
29. Jiménez-Nuñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326
30. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180
31. Simonneau, A.; Garcia, P.; Goddard, J.-P.; Mouries-Mansuy, V.; Malacria, M.; Fensterbank, L. Beilstein J. Org. Chem. 2011, 7, 1379
32. Leboeuf, D.; Simonneau, A.; Aubert, C.; Malacria, M.; Gandon, V.; Fensterbank, L. Angew. Chem., Int. Ed. 2011, 50, 6868
33. Harrak, Y.; Simonneau, A.; Malacria, M.; Gandon, V.; Fensterbank, L. Chem. Commun. 2010, 46, 865
34. Benedetti, E.; LemieÌre, G.; Chapellet, L.-L.; Penoni, A.; Palmisano, G.; Malacria, M.; Goddard, J.-P.; Fensterbank, L. Org. Lett. 2010, 12, 4396
35. LemieÌre, G.; Gandon, V.; Cariou, K.; Hours, A.; Fukuyama, T.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2009, 131, 2993
36. Diéz-Gonzalez, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612
37. Barbazanges, M.; Fensterbank, L. ChemCatChem 2012, 4, 1065 and references therein
38. El-Hellani, A.; Bour, C.; Gandon, V. Adv. Synth. Catal. 2011, 353, 1865
39. Alcarazo, M.; Stork, T.; Anoop, A.; Thiel, W.; Fürstner, A. Angew. Chem., Int. Ed. 2010, 49, 2542
40. Zeng, X.; Soleilhavoup, M.; Bertrand, G. Org. Lett. 2009, 11, 3166
41. Bartolomé, C.; Carrasco-Rando, M.; Coco, S.; Cordovilla, C.; Martín-Alvarez, J. M.; Espinet, P. Inorg. Chem. 2008, 47, 1616
42. Lavallo, V.; Frey, G. D.; Kousar, S.; Donnadieu, B.; Bertrand, G. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 13569
43. Bartolomé, C.; Carrasco-Rolando, M.; Coco, S.; Cordovilla, C.; Espinet, P.; Martín-Alvarez, J. M. Dalton Trans. 2007, 5339
44. Ricard, L.; Gagosz, F. Organometallics 2007, 26, 4704
45. Dembek, A. A.; Fagan, P. J. Organometallics 1996, 15, 1319
46. Dembek, A. A.; Fagan, P. J. Organometallics 1995, 14, 3741
47. Fagan, P. J.; Ward, M. D.; Calabrese, J. C. J. Am. Chem. Soc. 1989, 111, 1698
48. De Quadras, L.; Stahl, J.; Zhuravlev, F.; Gladysz, J. A. J. Organomet. Chem. 2007, 692, 1859
49. Schmidbaur, H.; Schier, A. Chem. Soc. Rev. 2012, 41, 370
50. Schmidbaur, H.; Schier, A. Chem. Soc. Rev. 2008, 37, 1931
51. Pyykkö, P. Chem. Soc. Rev. 2008, 37, 1967
52. Baenziger, N. C.; Bennett, W. E.; Soborofe, D. M. Acta Crystallogr. 1976, B32, 962
53. Barabé, F.; Levesque, P.; Korobkov, I.; Barriault, L. Org. Lett. 2011, 13, 5580
54. Benitez, D.; Tkatchouk, E.; Gonzalez, A. Z.; Goddard, W. A., III; Toste, F. D. Org. Lett. 2009, 11, 4798
55. Otto, S.; Roodt, A. Inorg. Chim. Acta 2004, 357, 1
56. Rose-Munch, F.; Cetiner, D.; Chavarot-Kerlidou, M.; Rose, E.; Agbossou-Niedercorn, F.; Chamoreau, L.-M.; Gontard, G. Organometallics 2011, 30, 3530
57. Muller, A.; Otto, S.; Roodt, A. Dalton Trans. 2008, 650
58. Allen, D. W.; March, L. A.; Nowell, I. W. J. Chem. Soc., Dalton Trans. 1984, 483
59. Allen, D. W.; Taylor, B. F. J. Chem. Soc., Dalton Trans. 1982, 51
60. Benitez, D.; Shapiro, N. D.; Tkatchouk, E.; Wang, Y.; Goddard, W. A., III; Toste, D. Nat. Chem. 2009, 1, 482
61. Clavier, H.; Nolan, S. P. Chem. Commun. 2010, 46, 841
62. Note that since the Ru atom is not implemented in Sambvca, it has been replaced by iodine, which has a quite close Bondi radius.
63. Lee, S. I.; Kim, S. M.; Choi, M. R.; Kim, S. Y.; Chung, Y. K. J. Org. Chem. 2006, 71, 9366
64. Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863
65. Watson, I. D. G.; Toste, F. D. Chem. Sci. 2012, 3, 2899
66. Marinetti, A.; Jullien, H.; Voituriez, A. Chem. Soc. Rev. 2012, 41, 4884
67. Lee, S. I.; Chatani, N. Chem. Commun. 2009, 371
68. Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326
69. Michelet, V.; Toullec, P. Y.; Geneît, J.-P. Angew. Chem., Int. Ed. 2008, 47, 4268
70. Wang, W.; Hammond, G. B.; Xu, B. J. Am. Chem. Soc. 2012, 134, 5697
71. 3AuCl was used)
72. Kobayashi, T.; Koga, Y.; Narasaka, K. J. Organomet. Chem. 2001, 624, 73
73. Blessing, R. H. Acta Crystallogr. 1995, A51, 33
74. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Crystallogr. 1993, 26, 343
75. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112
76. Chirality in Transition Metal Chemistry: Molecules, Supramolecular Assemblies and Materials; Amouri, H.; Gruselle, M., Eds.; Wiley: Chichester, U.K., 2008.
77. Dubarle-Offner, J.; Axet, M. R.; Chamoreau, L.-M.; Amouri, H. Organometallics 2012, 31, 4429