Intermolecular hydroamination of allenes with N-unsubstituted carbamates catalyzed by a gold(I) N-heterocyclic carbene complex

Organic Letters

Volumn 10, Issue 14, 2008, Pages 3157-3159

  Kinder, Robert E ^a   Zhang, Zhibin ^a   Widenhoefer, Ross A ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALLENE; BENZOIC ACID DERIVATIVE; CARBAMIC ACID DERIVATIVE; CARBENE; DRUG DERIVATIVE; METHANE; ORGANOGOLD COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKADIENES; BENZOATES; CARBAMATES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; METHANE; MOLECULAR STRUCTURE; ORGANOGOLD COMPOUNDS; STEREOISOMERISM;

EID: 52049119342     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8010858     Document Type: Article

References (66)

1. (a) Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689.
2. (b) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
3. (c) Hollis, T. K.; Overman, L. E. J. Organomet. Chem. 1999, 576, 290.
4. (d) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
5. For recent efforts directed toward the synthesis of allylic amines, see: (a) Singh, O. V.; Han, H. J. Am. Chem. Soc. 2007, 129, 774.
6. (b) Polet, D.; Alexakis, A.; Tissot-Croset, K.; Corminboeuf, C.; Ditrich, K. Chem. Eur. J. 2006, 12, 3596.
7. (c) Defieber, C.; Ariger, M. A.; Moriel, P.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 3139.
8. (d) Weiss, M. E.; Fischer, D. F.; Xin, Z.-q.; Jautze, S.; Schweizer, W. B.; Peters, R. Angew. Chem., Int. Ed. 2006, 45, 5694.
9. (e) Jautze, S.; Seiler, P.; Peters, R. Angew. Chem., Int. Ed. 2007, 46, 1260.
10. (f) Skucas, E.; Ngai, M.; Komanduri, V.; Krische, M. J. Acc. Chem. Res. 2007, 40, 1394.
11. (g) Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2008, 130, 3316.
12. (h) Fiori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2007, 129, 562.
13. (i) Liang, C.; Collet, F.; Robert-Peillard, F.; Muller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343.
14. (j) Matsui, K.; Takizawa, S.; Sasai, H. J. Am. Chem. Soc. 2005, 127, 3680.
15. (k) Shi, Y.-L.; Shi, M. Eur. J. Org. Chem. 2007, 2905.
16. The intermolecular hydroamination of 1,3-dienes has also been investigated as a route to allylic amines: (a) Qin, H.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M J. Am. Chem. Soc. 2006, 128, 1611.
17. (b) Brouwer, C.; He, C. Angew. Chem., Int. Ed. 2006, 45, 1744.
18. (c) Johns, A. M.; Liu, Z.; Hartwig, J. F. Angew. Chem., Int. Ed. 2007, 46, 7259.
19. (d) Johns, A. M.; Utsunomiya, M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 1828.
20. (e) Lober, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366.
21. (f) Baker, R.; Onions, A.; Popplestone, R. J.; Smith, T. N. J. Chem. Soc., Perkin Trans. 2 1975, 1133.
22. (g) Pawlas, J.; Nakao, Y.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 3669.
23. (h) Kiji, J.; Sasakawa, E.; Yamamoto, K.; Furukawa, J. J. Organomet. Chem. 1974, 77, 125.
24. (a) Volz, F.; Krause, N. Org. Biomol. Chem. 2007, 5, 1519.
25. (b) Morita, N.; Krause, N. Eur. J. Org. Chem. 2006, 4634.
26. (c) Morita, N.; Krause, N. Org. Lett. 2004, 6, 4121.
27. (d) Hoover, J. M.; Petersen, J. R.; Pikul, J. H.; Johnson, A. R. Organometallics 2004, 23, 4614.
28. (e) Zhang, Z.; Bender, C. F.; Widenhoefer, R. A. Org. Lett. 2007, 9, 2887.
29. (f) LaLonde, R. L.; Sherry, B. D.; Kang, E. J.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 2452.
30. (g) Lee, P. H.; Kim, H.; Lee, K.; Kim, M.; Noh, K.; Kim, H.; Seomoon, D. Angew. Chem., Int. Ed. 2005, 44, 1840.
31. (h) Meguro, M.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 5421.
32. (i) Patil, N. T.; Lutete, L. M.; Nishina, N.; Yamamoto, Y. Tetrahedron Lett. 2006, 47, 4749.
33. (j) Claesson, A.; Sahlberg, C.; Luthman, K. Acta Chem. Scand. 1979, 309.
34. (k) Huby, N. J. S.; Kinsman, R. G.; Lathbury, D.; Vernon, P. G.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1991, 145.
35. (l) Gallagher, T.; Jones, S. W.; Mahon, M. F.; Molloy, K. C. J. Chem. Soc., Perkin Trans. 1 1991, 2193.
36. (m) Ha, J. D.; Cha, J. K. J. Am. Chem. Soc. 1999, 121, 10012.
37. (n) Arredondo, V. M.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 4871.
38. (o) Hong, S.; Kawaoka, A. M.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 15878.
39. (p) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475.
40. (q) Ackermann, L.; Bergman, R. G.; Loy, R. N. J. Am. Chem. Soc. 2003, 125, 11956.
41. Zhang, Z.; Liu, C.; Kinder, R. E.; Han, X.; Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2006, 128, 9066.
42. (a) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923.
43. (b) Ayinla, R. O.; Schafer, L. L. Inorg. Chim. Acta 2006, 359, 3097.
44. (c) Besson, L.; Gore, J.; Cazes, B. Tetrahedron Lett. 1995, 36, 3857.
45. (d) Nishina, N.; Yamamoto, Y. Angew. Chem., Int. Ed. 2006, 45, 3314.
46. (e) Nishina, N.; Yamamoto, Y. Synlett 2007, 1767.
47. 2, led to formation of mixtures of mono- and bisaddition products: Al-Masum, M.; Meguro, M.; Yamamoto, Y. Tetrahedron Lett. 1997, 38, 6071.
48. Zhang, Z.; Widenhoefer, R. A. Org. Lett. 2008, 10, 2079.
49. For additional examples of intermolecular allene hydrofunctionalization, see: (a) Patil, N. T.; Pahadi, N. K.; Yamamoto, Y. Can. J. Chem. 2005, 83, 569.
50. (b) Kim, I. S.; Krische, M. J. Org. Lett. 2008, 10, 513.
51. (c) Schulz, M.; Teles, J. H. Chem. Abstr. 1997, 127, 121499; (BASF AG), WO-A1 9721648, 1997.
52. (d) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156.
53. (e) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019.
54. (f) Yamamoto, Y.; Al-Masum, M.; Fujiwara, N.; Asao, N. Tetrahedron Lett. 1995, 36, 2811.
55. (g) Yamamoto, Y.; Al-Masum, M. Synlett 1995, 969.
56. (h) Yamamoto, Y.; Al-Masum, M.; Takeda, A. Chem. Commun. 1996, 831.
57. (i) Yamamoto, Y.; Al-Masum, M.; Fujiwara, N. Chem. Commun. 1996, 381.
58. (j) Besson, L.; Gore, J.; Cazes, B. Tetrahedron Lett. 1995, 36, 3853.
59. (k) Al-Masum, M.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 3809.
60. It appears unlikely that these regiochemical differences can be attributed soley to the steric profile of the respective nucleophiles as reaction of 3 with 2-phenyl-1-ethanol catalyzed by (2)AuCl/AgOTf led to formation of a 4.4:1 mixture of 3-methyl-1-phenethoxy-2-butene and 1,1-dimethyl-1-phenethoxy-2-propene: Zhang, Z.; Widenhoefer, R. A. Unpublished results.
61. (a) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526.
62. (b) Zhang, J.; Yang, C.-G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798.
63. (c) Hashmi, A. S. K.; Weyrauch, J. P.; Frey, W.; Bats, J. W. Org. Lett. 2004, 6, 4391.
64. (d) Liu, Y.; Song, F.; Song, Z.; Liu, M.; Yan, B. Org. Lett. 2005, 7, 5409.
65. Kovács, G.; Ujaque, G.; Lledós, A. J. Am. Chem. Soc. 2008, 130, 853.
66. Zhang, Z.; Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2007, 129, 14148.