Uranium(III)-mediated C-C-coupling of terminal alkynes: Formation of dinuclear uranium(IV) vinyl complexes

Journal of the American Chemical Society

Volumn 134, Issue 30, 2012, Pages 12792-12797

  Kosog, Boris ^a   Kefalidis, Christos E ^b   Heinemann, Frank W ^a   Maron, Laurent ^b   Meyer, Karsten ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b INSA   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1-HEXYNE; ADAMANTANES; DFT CALCULATION; DINUCLEAR; HYDROAMINATIONS; HYDROCARBON FRAGMENTS; TERMINAL ALKYNE; TRANSITION STATE; VINYL COMPLEXES;

ACETYLENE; AROMATIC HYDROCARBONS; BUTADIENE; DENSITY FUNCTIONAL THEORY; URANIUM;

URANIUM COMPOUNDS;

1,6 HEPTADIYNE; 1,7 OCTADIYNE; ADAMANTANE; ALKYNE; CYCLOHEXANE; ETHYLENE GLYCOL DIMETHYL ETHER; HYDROCARBON; UNCLASSIFIED DRUG; URANIUM DERIVATIVE;

AMINATION; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; CROSS COUPLING REACTION; DENSITY FUNCTIONAL THEORY; ISOMERIZATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84864436681     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3047393     Document Type: Article

References (70)

1. Werner, H.; Schäfer, M.; Wolf, J.; Peters, K.; von Schnering, H. G. Angew. Chem., Int. Ed. 1995, 34, 191
2. Sylvester, K. T.; Chirik, P. J. J. Am. Chem. Soc. 2009, 131, 8772
3. Yi, C. S.; Liu, N. Synlett 1999, 1999, 281
4. Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 43, 3795
5. Shibata, Y.; Tanaka, K. Synthesis 2012, 323
6. For selected reviews on catalytic gold(I) chemistry see: Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180
7. Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395
8. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239
9. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351
10. Widenhoefer, R. A. Chem.-Eur. J. 2008, 14, 5382
11. Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326
12. Arcadi, A. Chem. Rev. 2008, 108, 3266
13. Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208
14. Pradal, A.; Toullec, P. Y.; Michelet, V. Synthesis 2011, 1501
15. Corma, A.; Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111, 1657
16. Aubert, C.; Fensterbank, L.; Garcia, P.; Malacria, M.; Simonneau, A. Chem. Rev. 2011, 111, 1954
17. Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994
18. Bandini, M. Chem. Soc. Rev. 2011, 40, 1358
19. Boorman, T. C.; Larrosa, I. Chem. Soc. Rev. 2011, 40, 1910
20. Campbell, M. J.; Toste, F. D. Chem. Sci. 2011, 2, 1369
21. Rudolph, M.; Hashmi, A. S. K. Chem. Commun. 2011, 47, 6536
22. Weber, D.; Jones, T. D.; Adduci, L. L.; Gagné, M. R. Angew. Chem., Int. Ed. 2012, 51, 2452 and references therein
23. Hashmi, A. Gold Bull. 2009, 42, 275
24. Schmidbaur, H.; Schier, A. Organometallics 2009, 29, 2
25. Hashmi, A. S. K. Angew. Chem., Int. Ed. 2010, 49, 5232
26. Raubenheimer, H. G.; Schmidbaur, H. S. Afr. J. Sci. 2011, 107, 1
27. Weber, D.; Tarselli, M. A.; Gagné, M. R. Angew. Chem., Int. Ed. 2009, 48, 5733
28. Weber, D.; Gagné, M. R. Org. Lett. 2009, 11, 4962
29. Tkatchouk, E.; Mankad, N. P.; Benitez, D.; Goddard, W. A.; Toste, F. D. J. Am. Chem. Soc. 2011, 133, 14293
30. Evans, W. J.; Davis, B. L. Chem. Rev. 2002, 102, 2119
31. Zimmermann, M.; Anwander, R. Chem. Rev. 2010, 110, 6194 and references therein
32. Marks, T. J. Science 1982, 217, 989
33. Fox, A. R.; Bart, S. C.; Meyer, K.; Cummins, C. C. Nature 2008, 455, 341
34. Haskel, A.; Straub, T.; Eisen, M. S. Organometallics 1996, 15, 3773
35. Wang, J. Q.; Dash, A. K.; Berthet, J. C.; Ephritikhine, M.; Eisen, M. S. Organometallics 1999, 18, 2407
36. Dash, A. K.; Wang, J. X.; Berthet, J. C.; Ephritikhine, M.; Eisen, M. S. J. Organomet. Chem. 2000, 604, 83
37. Straub, T.; Haskel, A.; Neyroud, T. G.; Kapon, M.; Botoshansky, M.; Eisen, M. S. Organometallics 2001, 20, 5017
38. Barnea, E.; Andrea, T.; Kapon, M.; Berthet, J.-C.; Ephritikhine, M.; Eisen, M. S. J. Am. Chem. Soc. 2004, 126, 10860
39. Barnea, E.; Moradove, D.; Berthet, J.-C.; Ephritikhine, M.; Eisen, M. S. Organometallics 2005, 25, 320
40. Barnea, E.; Andrea, T.; Berthet, J.-C.; Ephritikhine, M.; Eisen, M. S. Organometallics 2008, 27, 3103
41. Tsutsui, M.; Ely, N.; Gebala, A. Inorg. Chem. 1975, 14, 78
42. Tsutsui, M.; Ely, N.; Dubois, R. Acc. Chem. Res. 1976, 9, 217
43. Dormond, A.; Aaliti, A.; Elbouadili, A.; Moise, C. J. Organomet. Chem. 1987, 329, 187
44. Van der Sluys, W. G.; Burns, C. J.; Sattelberger, A. P. Organometallics 1989, 8, 855
45. Weydert, M.; Brennan, J. G.; Andersen, R. A.; Bergman, R. G. Organometallics 1995, 14, 3942
46. Castro-Rodriguez, I.; Nakai, H.; Gantzel, P.; Zakharov, L. N.; Rheingold, A. L.; Meyer, K. J. Am. Chem. Soc. 2003, 125, 15734
47. Fortier, S.; Melot, B. C.; Wu, G.; Hayton, T. W. J. Am. Chem. Soc. 2009, 131, 15512
48. Duhović, S.; Monreal, M. J.; Diaconescu, P. L. Inorg. Chem. 2010, 49, 7165
49. Hayes, C. E.; Leznoff, D. B. Organometallics 2010, 29, 767
50. Fortier, S.; Walensky, J. R.; Wu, G.; Hayton, T. W. J. Am. Chem. Soc. 2011, 133, 11732
51. Cramer, R. E.; Panchanatheswaran, K.; Gilje, J. W. J. Am. Chem. Soc. 1984, 106, 1853
52. Nakai, H.; Hu, X.; Zakharov, L. N.; Rheingold, A. L.; Meyer, K. Inorg. Chem. 2004, 43, 855
53. Arnold, P. L. Nature Chem. 2009, 1, 29
54. Cantat, T.; Arliguie, T.; Noël, A.; Thuéry, P.; Ephritikhine, M.; Floch, P. L.; Mézailles, N. J. Am. Chem. Soc. 2009, 131, 963
55. Cooper, O. J.; Mills, D. P.; McMaster, J.; Moro, F.; Davies, E. S.; Lewis, W.; Blake, A. J.; Liddle, S. T. Angew. Chem., Int. Ed. 2011, 50, 2383
56. Fortier, S.; Walensky, J. R.; Wu, G.; Hayton, T. W. J. Am. Chem. Soc. 2011, 133, 6894
57. Ma, G.; Ferguson, M. J.; McDonald, R.; Cavell, R. G. Inorg. Chem. 2011, 50, 6500
58. Straub, T.; Frank, W.; Reiss, G. J.; Eisen, M. S. J. Chem. Soc., Dalton Trans. 1996, 2541
59. Newell, B. S.; Rappe, A. K.; Shores, M. P. Inorg. Chem. 2010, 49, 1595
60. Matson, E. M.; Fanwick, P. E.; Bart, S. C. Organometallics 2011, 30, 5753
61. Fox, A. R.; Creutz, S. E.; Cummins, C. C. Dalton Trans. 2010, 39, 6632
62. Evans, W. J.; Meadows, J. H.; Hunter, W. E.; Atwood, J. L. J. Am. Chem. Soc. 1984, 106, 1291
63. Evans, W. J.; Champagne, T. M.; Ziller, J. W. J. Am. Chem. Soc. 2006, 128, 14270
64. Lam, O. P.; Bart, S. C.; Kameo, H.; Heinemann, F. W.; Meyer, K. Chem. Commun. 2010, 46, 3137
65. Lam, O. P.; Heinemann, F. W.; Meyer, K. Chem. Sci. 2011, 2, 1538
66. Lam, O. P.; Heinemann, F. W.; Meyer, K. Angew. Chem., Int. Ed. 2011, 50, 5965
67. Castro, L.; Lam, O. P.; Bart, S. C.; Meyer, K.; Maron, L. Organometallics 2010, 29, 5504
68. Yahia, A.; Castro, L.; Maron, L. Chem.-Eur. J. 2010, 16, 5564
69. Lam, O. P.; Castro, L.; Kosog, B.; Heinemann, F. W.; Maron, L.; Meyer, K. Inorg. Chem. 2012, 51, 781
70. Labouille, S.; Nief, F.; Maron, L. J. Phys. Chem. A 2011, 115, 8295