Experimental and computational evidence for gold vinylidenes: Generation from terminal alkynes via a bifurcation pathway and facile C-H insertions

Journal of the American Chemical Society

Volumn 134, Issue 1, 2012, Pages 31-34

  Ye, Longwu ^a   Wang, Yanzhao ^a   Aue, Donald H ^a   Zhang, Liming ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C-H INSERTION; CYCLOISOMERIZATIONS; GOLD CATALYSTS; GOOD YIELD; MECHANISTIC STUDIES; N-H INSERTION; PYRIDINE N-OXIDE; REACTION PATHWAYS; TERMINAL ALKYNE; THEORETICAL CALCULATIONS; WEAK BASE;

ACETYLENE; GOLD; POLYCYCLIC AROMATIC HYDROCARBONS; REACTION INTERMEDIATES; RHODIUM;

GOLD COMPOUNDS;

(2 ETHYNYLPHENYL)ALKYNE; ALKYNE DERIVATIVE; GOLD; GOLD VINYLIDENE; PYRIDINE 1 OXIDE; RUTHENIUM; UNCLASSIFIED DRUG; VINYLIDENE CHLORIDE;

ARTICLE; CALCULATION; CATALYST; CONTROLLED STUDY; FACILE CYCLOISOMERIZATION; ISOMERIZATION; REACTION ANALYSIS; THEORETICAL MODEL;

ALKYNES; CARBON; HYDROGEN; INDENES; ISOMERISM; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOGOLD COMPOUNDS; THERMODYNAMICS; VINYL COMPOUNDS;

EID: 84862908729     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2091992     Document Type: Article

References (51)

1. Corma, A.; Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111, 1657
2. Wang, S.; Zhang, G.; Zhang, L. Synlett 2010, 692
3. Abu Sohel, S. M.; Liu, R.-S. Chem. Soc. Rev. 2009, 38, 2269
4. Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395
5. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239
6. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351
7. Arcadi, A. Chem. Rev. 2008, 108, 3266
8. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180
9. Fürstner, A.; Davis, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410
10. Hashmi, A. S. K.; Rudolph, M. Chem. Soc. Rev. 2008, 37, 1766
11. Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208
12. Metal Vinylidenes and Allenylidenes in Catalysis: From Reactivity to Applications in Synthesis; Bruneau, C.; Dixneuf, P. H., Eds.; Wiley-VCH: Weinheim, Germany, 2008.
13. Lynam, J. M. Chem.-Eur. J. 2010, 16, 8238
14. Trost, B. M.; McClory, A. Chem.-Asian J. 2008, 3, 164
15. Bruneau, C.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2006, 45, 2176
16. Varela, J. A.; Saá, C. Chem.-Eur. J. 2006, 12, 6450
17. McDonald, F. E. Chem.-Eur. J. 1999, 5, 3103
18. Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311
19. Bruce, M. I. Chem. Rev. 1991, 91, 197
20. Seregin, I. V.; Schammel, A. W.; Gevorgyan, V. Tetrahedron 2008, 64, 6876
21. Lavallo, V.; Frey, G. D.; Kousar, S.; Donnadieu, B.; Bertrand, G. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 13569
22. Seregin, I. V.; Gevorgyan, V. J. Am. Chem. Soc. 2006, 128, 12050
23. Mamane, V.; Hannen, P.; Fürstner, A. Chem.-Eur. J. 2004, 10, 4556
24. Xia, Y.; Dudnik, A. S.; Li, Y.; Gevorgyan, V. Org. Lett. 2010, 12, 5538
25. Rabaâ, H.; Engels, B.; Hupp, T.; Hashmi, A. S. K. Int. J. Quantum Chem. 2007, 107, 359
26. Soriano, E.; Marco-Contelles, J. Organometallics 2006, 25, 4542
27. Ye, L.; He, W.; Zhang, L. Angew. Chem., Int. Ed. 2011, 50, 3236
28. He, W.; Li, C.; Zhang, L. J. Am. Chem. Soc. 2011, 8482
29. Ye, L.; He, W.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 8550
30. Ye, L.; Cui, L.; Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 3258
31. Lu, B.; Li, C.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 14070
32. Fors, B. P.; Watson, D. A.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 13552
33. Lian, J. J.; Chen, P. C.; Lin, Y. P.; Ting, H. C.; Liu, R. S. J. Am. Chem. Soc. 2006, 128, 11372
34. Lin, G. Y.; Yang, C. Y.; Liu, R. S. J. Org. Chem. 2007, 72, 6753
35. Bavaresco, L.; Vezzulli, S. Rec. Prog. Med. Plants 2006, 11, 389
36. Buchanan, G. O.; Williams, P. G.; Feling, R. H.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Org. Lett. 2005, 7, 2731
37. Jakubowski, J. A.; Utterback, B. G.; Mais, D. E.; Hardinger, S. A.; Braish, T. F.; Nevill, C. R.; Fuchs, P. L. Prostaglandins 1994, 47, 189
38. Tomyama, T.; Ikegami, S.; Hashimoto, S.; Imamaki, T. Jpn. Kokai Tokkyo Koho JP 07076550 A 19950320, 1995.
39. Ratilainen, J.; Huhtala, P.; Karjalainen, A.; Karjalainen, A.; Haapalinna, A.; Virtanen, R.; Lehtimaeki, J. PCT Int. Appl., WO2001085698 A1 20011115, 2001
40. Burkhard, R. K.; Sellers, D. E.; DeCou, F.; Lambert, J. L. J. Org. Chem. 1959, 24, 767
41. Taduri, B. P.; Ran, Y.-F.; Huang, C.-W.; Liu, R.-S. Org. Lett. 2006, 8, 883
42. Cheong, P. H. Y.; Morganelli, P.; Luzung, M. R.; Houk, K. N.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 4517
43. Chen, K.-H.; Feng, Y. J.; Ma, H.-W.; Lin, Y.-C.; Liu, Y.-H.; Kuo, T.-S. Organometallics 2010, 29, 6829
44. Bhunia, S.; Liu, R.-S. J. Am. Chem. Soc. 2008, 130, 16488
45. Horino, Y.; Yamamoto, T.; Ueda, K.; Kuroda, S.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 2809
46. Lemiere, G.; Gandon, V.; Cariou, K.; Hours, A.; Fukuyama, T.; Dhimane, A. L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2009, 131, 2993
47. Benitez, D.; Tkatchouk, E.; Gonzalez, A. Z.; Goddard, W. A., III; Toste, F. D. Org. Lett. 2009, 11, 4798
48. Ess, D. H.; Wheeler, S. E.; Iafe, R. G.; Xu, L.; Çelebi- Ölçüm, N.; Houk, K. N. Angew. Chem., Int. Ed. 2008, 47, 7592
49. Noey, E. L.; Wang, X.; Houk, K. N. J. Org. Chem. 2011, 76, 3477
50. Garayalde, D.; Gómez-Bengoa, E.; Huang, X.; Goeke, A.; Nevado, C. J. Am. Chem. Soc. 2010, 132, 4720
51. Wang, Z. J.; Benitez, D.; Tkatchouk, E.; Goddard, W. A., III; Toste, F. D. J. Am. Chem. Soc. 2010, 132, 13064