Cobalt(II)-catalyzed intermolecular benzylic C-H amination with 2,2,2-trichloroethoxycarbonyl azide (TrocN3)

Organometallics

Volumn 29, Issue 2, 2010, Pages 389-393

  Lu, Hongjian ^a   Subbarayan, Velusamy ^a   Tao, Jingran ^a   Zhang, X Peter ^a  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIC; C-H BOND; HIGH YIELD; METALLOPORPHYRINS; NITRENE INSERTIONS; NITRENES; NITROGEN GAS;

AMINATION; COBALT; PORPHYRINS;

AMINES;

EID: 74549198653     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900916g     Document Type: Article

References (55)

1. (a) Modern Amination Methods; Racci, A., Ed.; Willey-VCH: Weinheim, 2000.
2. (b) Salvatore, R.N.; Yoon, C. H,; Jung, K. W. Tetrahedron 2001, 57, 7785.
3. (c) Johannsen, M.; Jorgensen, A. Chem. Rev. 1998, 95, 1689.
4. (d) Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
5. (a) Muller, P.; Fruit, V. Chem. Rev. 2003, 103, 2905.
6. (b) Dauban, P.; Dodd, R. H. Synlett 2003, 1571.
7. (c) Koser, G. F. Top. Curr. Chem. 2003, 224, 137.
8. (d) Halfen, J. A. Curr. Org. Chem. 2005, 9, 657.
9. For recent reviews, see: (a) Espino, C. G.; Du Bois, J. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005; pp 379-416.
10. (b) Davies, H, M. L. Angew. Chem., Int. Ed. 2006, 45, 6422.
11. (c) Davies, H. M. L.; Manning, J. R. Nature 2008, 457, 417.
12. For select recent examples of intermolecular C-H animation with ArI=NTs, see: (a) Many, J.-P.; Bedi, G.; Battioni, P.; Mansuy, D. New J. Chem. 1989, 13, 651.
13. (b) Nageli, I.; Baud, C.; Bernardinelli, G.; Jacquier, Y; Moran, M.; Muller, P. Helv. Chim. Acta 1997, 80, 1087.
14. (c) Au, S.-.M.; Huang, J.-S.; Che, C-M.; Yu, W.-Y. J. Org. Chem. 2000, 65, 7858.
15. (d) Yang, J.; Weinberg, R.; Breslow, R. Chem. Commun. 2000, 531.
16. (e) Yamawaki, M.; Tsutsui, H.; Kitagaki, S.; Anada, M.; Hashimoto, S. Tetrahedron Lett. 2002, 43, 9561.
17. (f) Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem-Eur. J. 2002, 8, 1563.
18. (g) Fruetos, M. R.; Trofimenko, S.; Diaz-Requejo, M. M.; Perez, P. J. J. Am. Chem. Soc. 2006, 128, 11784.
19. (h) Li, Z.; Capretto, D. A.; Rahaman, R.; He, C. Angew. Chem., Int. Ed. 2007, 46, 5184.
20. (i) Chang, J. W. W.; Chan, P. W. H. Angew. Chem., Int. Ed. 2008, 47, 1138.
21. For select recent examples of intermolecular C-H animation with in situ generated ArI=NTs, see: (a) Yu, X.-Q.; Huang, J.-S.; Zhou, X.-G.; Che, C.-M. Org. Lett. 2000, 2, 2233.
22. (b)Reddy, R.P.; Davies, H. M. L. Org. Lett. 2006, 8, 5013.
23. (c) Fiori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2007, 129, 562.
24. (d) He, L.; Yu, J.; Zhang, J.; Yu, X.-Q. Org. Lett. 2007, 9, 2277.
25. (e) Chan, J.; Baucom, K. D.; Murry, J. A. J. Am. Chem. Soc. 2007, 129, 14106.
26. (f) Liang, C.; Collet, F.; Robert-Peillard, F.; Muller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc 2008, 130, 343.
27. (g) Wang, Z.; Zhang, Y.; Fu, H.; Jiang, Y. Zhao, Y. Org. Lett. 2008, 10, 1863.
28. (a) Chanda, B. M.; Vyas, R.; Bedekar, A. V. J. Org. Chem. 2001, 66, 30.
29. (b) Albone, D. P.; Challenger, S.; Derrick, A. M.; Fillery, S. M.; Irwin, J. L.; Parsons, C. M.; Takada, H.; Taylor, P. C.; Wilson, D. J. Org. Biomol. Chem. 2005, 3, 107.
30. (c) Bhuyan, R.; Nicholas, K. M. Org. Lett. 2007, 9, 3957.
31. (a) Lebel, H.; Huard, K.; Lectard, S. J. Am. Chem. Soc. 2005, 127, 14198.
32. (b) Lebel, H.; Leogane, O.; Huard, K.; Lectard, S. Pure Appl. Chem. 2006, 78, 363.
33. (c) Lebel, H.; Huard, K. Org. Lett. 2007, 9, 639.
34. (a) Cenini, S.; Gallo, E.; Penoni, A.; Ragaini, F.; Tollari, S. Chem Commun. 2000, 2265.
35. (b) Ragaini, F.; Penoni, A.; Gallo, E.; Tollari, S.; Gotti, C. L.; Lapadula, M.; Mangioni, E.; Cenini, S. Chem.-Eur. J. 2003, 9, 249.
36. (c) Omura, K.; Murakami, M.; Uchida, T.; Irie, R.; Katsuki, T. Chem. Lett. 2003, 32, 354.
37. (d) Stokes, B. J.; Dong, H.; Leslie, B. E.; Pumphrey, A. L.; Driver, T. G. J. Am. Chem. Soc 2007, 129, 7500.
38. (e) Shen, M.; Leslie, B. E.; Driver, T. G. Angew. Chem., Int. Ed. 2008, 47, 5056.
39. (f) Badiei, Y. M.; Dinescu, A.; Dai, X.; Palomino, R. M.; Heinemann, F. W.; Cundari, T. R.; Warren, T. H. Angew. Chem., Int. Ed. 2008, 47, 9961.
40. (a) Harden, J. D.; Ruppel, J. V.; Gao, G.-Y.; Zhang, X. P. Chem. Org. 2007, 4644.
41. (b) Vyas, R.; Gao, G.-Y.; Harden, J. D.; Zhang, X. P. Org. Lett. 2004, 6, 1907.
42. (c) Gao, G.-Y.; Harden, J. D.; Zhang, X. P. Org. Lett. 2005, 7, 3191
43. (a) Ruppel, J. V.; Kamble, R. M.; Zhang, X. P. Org. Lett. 2007, 9, 4889.
44. (b) Gao, G.-Y.; Jones, J. E.; Vyas, R.; Harden, J. D.; Zhang, X. P. J. Org. Chem. 2006, 71, 6655.
45. (c) Ruppel, J. V.; Jones, J. E.; Huff, C. A.; Kamble, R. M.; Chen, Y.; Zhang, X. P. Org. Lett. 2008, 10, 1995.
46. (d) Jones, J. E.; Ruppel, J. V.; Gao, G.-Y.; Moore, T. M.; Zhang, X. P. J. Org. Chem. 2008, 73, 7260.
47. (e) Subbarayan, V.; Ruppel, J. V.; Zhu, S.; Perman, J. A.; Zhang, X. P. Chem. Commun. 2009, 4266.
48. 3 was previously used for a Ru-catalyzed sulfimidation process; see: Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301.
49. Under similar conditions, use of a porphyrin complex of the second-row transition metal ruthenium, Ru(TPP)(CO), could produce 2a in 79% yield.
50. The current catalytic system appeared to be ineffective for primary benzylic C-H bonds (such as toluene) and non-benzylic C-H bonds (such as cyclohexane). Reactions with tertiary benzylic C-H bonds gave the desired products in much lower yields.
51. Waser, J.; Gaspar, B.; Nambu, H.; Carreira, E. M. J. Am. Chem. Soc. 2006, 128, 11693.
52. Kim, S. H.; Jung, D. Y.; Chang, S. J. Org. Chem. 2007, 72, 9769.
53. Liu, J.; Mandel, S.; Hadad, C. M.; Platz, M. S. J. Org. Chem. 2004, 69, 8583.
54. Holzinger, M.; Abraham, J.; Whelan, P.; Graupner, R.; Ley, L.; Hennrich, F.; Kappes, M.; Hirsch, A. J. Am. Chem. Soc 2003, 125, 8566.
55. Uchida, T.; Tamura, Y.; Ohba, M.; Katsuki, T. Tetrahedron Lett. 2003, 44, 7965.