Combining gold(I)/gold(III) catalysis and C-H functionalization: A formal intramolecular [3+2] annulation towards tricyclic indolines and mechanistic studies

Angewandte Chemie - International Edition

Volumn 50, Issue 19, 2011, Pages 4450-4454

  Zhang, Guozhu ^a   Luo, Yingdong ^a   Wang, Yanzhao ^a   Zhang, Liming ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

gold; homogeneous catalysis; nitrogen heterocycles; oxidation; reaction mechanisms

Indexed keywords

C-H FUNCTIONALIZATION; CHLOROMETHYL; GOLD RUSH; H-BONDS; HOMOGENEOUS CATALYSIS; IN-SITU; MECHANISTIC STUDIES; NITROGEN HETEROCYCLES; OXIDATIVE COUPLINGS; REACTION MECHANISMS; SELECTFLUOR; TETRAFLUOROBORATES; VINYL GROUP;

CATALYSIS; GOLD COMPOUNDS; OXIDATION; REACTION KINETICS;

GOLD;

EID: 79955510598     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201100293     Document Type: Article

References (49)

1. P. Garcia, M. Malacria, C. Aubert, V. Gandon, L. Fensterbank, ChemCatChem 2010, 2, 493.
2. T. Lauterbach, M. Livendahl, A. Rosellõn, P. Espinet, A. M. Echavarren, Org. Lett. 2010, 12, 3006.
3. A. Kar, N. Mangu, H. M. Kaiser, M. Beller, M. K. Tse, Chem. Commun. 2008, 386
4. H. Wegner, S. Ahles, M. Neuburger, Chem. Eur. J. 2008, 14, 11310
5. S. Carrettin, J. Guzman, A. Corma, Angew. Chem. 2005, 117, 2282
6. Angew. Chem. Int. Ed. 2005, 44, 2242.
7. A. K. Sahoo, Y. Nakamura, N. Aratani, K. S. Kim, S. B. Noh, H. Shinokubo, D. Kim, A. Osuka, Org. Lett. 2006, 8, 4141
8. A. S. K. Hashmi, M. C. Blanco, D. Fischer, J. W. Bats, Eur. J. Org. Chem. 2006, 1387
9. Y. Fuchita, Y. Utsunomiya, M. Yasutake, J. Chem. Soc. Dalton Trans. 2001, 2330
10. A. S. K. Hashmi, T. D. Ramamurthi, F. Rominger, J. Organomet. Chem. 2009, 694, 592.
11. G. Zhang, Y. Peng, L. Cui, L. Zhang, Angew. Chem. 2009, 121, 3158
12. Angew. Chem. Int. Ed. 2009, 48, 3112
13. Y. Peng, L. Cui, G. Zhang, L. Zhang, J. Am. Chem. Soc. 2009, 131, 5062.
14. L. Cui, G. Zhang, L. Zhang, Bioorg. Med. Chem. Lett. 2009, 19, 3884.
15. P. T. Nyffeler, S. G. Durõn, M. D. Burkart, S. P. Vincent, C. H. Wong, Angew. Chem. 2005, 117, 196
16. Angew. Chem. Int. Ed. 2005, 44, 192
17. S. Stavber, M. Zupan, Acta Chim. Slov. 2005, 52, 13.
18. M. N. Hopkinson, J. E. Ross, G. T. Giuffredi, A. D. Gee, V. Gouverneur, Org. Lett. 2010, 12, 4904
19. T. de Haro, C. Nevado, J. Am. Chem. Soc. 2010, 132, 1512
20. A. Iglesias, K. Muñiz, Chem. Eur. J. 2009, 15, 10563
21. J. Brand, J. Charpentier, J. Waser, Angew. Chem. 2009, 121, 9510
22. Angew. Chem. Int. Ed. 2009, 48, 9346.
23. G. Zhang, L. Cui, Y. Wang, L. Zhang, J. Am. Chem. Soc. 2010, 132, 1474.
24. W. E. Brenzovich, D. Benitez, A. D. Lackner, H. P. Shunatona, E. Tkatchouk, W. A. Goddard, F. D. Toste, Angew. Chem. 2010, 122, 5651
25. Angew. Chem. Int. Ed. 2010, 49, 5519.
26. A. D. Melhado, W. E. Brenzovich, A. D. Lackner, F. D. Toste, J. Am. Chem. Soc. 2010, 132, 8885.
27. L. T. Ball, M. Green, G. C. Lloyd-Jones, C. A. Russell, Org. Lett. 2010, 12, 4724
28. W. E. Brenzovich, J.-F. Brazeau, F. D. Toste, Org. Lett. 2010, 12, 4728.
29. R. Giri, B.-F. Shi, K. M. Engle, N. Maugel, J.-Q. Yu, Chem. Soc. Rev. 2009, 38, 3242
30. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074
31. S. R. Klei, K. L. Tan, J. T. Golden, C. M. Yung, R. K. Thalji, K. A. Ahrendt, J. A. Ellman, T. D. Tilley, R. G. Bergman, ACS Symp. Ser. 2004, 885, 46.
32. A. S. K. Hashmi, S. Schafer, M. Wolfle, C. D. Gil, P. Fischer, A. Laguna, M. C. Blanco, M. C. Gimeno, Angew. Chem. 2007, 119, 6297
33. Angew. Chem. Int. Ed. 2007, 46, 6184.
34. M. Hopkinson, A. Tessier, A. Salisbury, G. Giuffredi, L. Combettes, A. Gee, V. Gouverneur, Chem. Eur. J. 2010, 16, 4739.
35. C. F. Rosewall, P. A. Sibbald, D. V. Liskin, F. E. Michael, J. Am. Chem. Soc. 2009, 131, 9488.
36. C. E. Houlden, C. D. Bailey, J. Gair Ford, M. R. Gagne, G. C. Lloyd-Jones, K. I. Booker-Milburn, J. Am. Chem. Soc. 2008, 130, 10066.
37. J. Ackermann, K. Amrein, B. Kuhn, A. V. Mayweg, W. Neidhart, PCT Int. Appl. WO 2009132986A1 20091105, 2009.
38. T. P. Zabawa, S. R. Chemler, Org. Lett. 2007, 9, 2035.
39. N. Mézailles, L. Ricard, F. Gagosz, Org. Lett. 2005, 7, 4133.
40. E. Wenkert, E. L. Michelotti, C. S. Swindell, M. Tingoli, J. Org. Chem. 1984, 49, 4894
41. V. Percec, J.-Y. Bae, D. H. Hill, J. Org. Chem. 1995, 60, 1060
42. Y. Kubota, S. Nakada, Y. Sugi, Synlett 1998, 183.
43. H. Li, R. A. Widenhoefer, Org. Lett. 2009, 11, 2671
44. Z. Zhang, C. Liu, R. E. Kinder, X. Han, H. Qian, R. A. Widenhoefer, J. Am. Chem. Soc. 2006, 128, 9066.
45. R. L. LaLonde, J. W. E. Brenzovich, D. Benitez, E. Tkatchouk, K. Kelley, I. I. I. W. A. Goddard, F. D. Toste, Chem. Sci. 2010, 1, 226.
46. A likely mechanism for the ligand exchange is outlined below
47. P. Lu, T. C. Boorman, A. M. Z. Slawin, I. Larrosa, J. Am. Chem. Soc. 2010, 132, 5580.
48. D. B. Denney, P. P. Klemchuk, J. Am. Chem. Soc. 1958, 80, 3285
49. D. B. Denney, P. P. Klemchuk, J. Am. Chem. Soc. 1958, 80, 6014.