Carbon-nitrogen bond-forming reactions of palladacycles with hypervalent iodine reagents

Organometallics

Volumn 26, Issue 6, 2007, Pages 1365-1370

  Dick, Allison R ^a   Remy, Matthew S ^a   Kampf, Jeff W ^a   Sanford, Melanie S ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C-N CHELATING LIGANDS; INSERTION REACTIONS; METAL CENTERS;

ACETIC ACID; BENZENE; CHEMICAL BONDS; LIGANDS; NITROGEN COMPOUNDS;

PALLADIUM COMPOUNDS;

EID: 33947689674     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om061052l     Document Type: Article

References (58)

1. For a review on Pd-catalyzed animation of aryl halides, see: Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131-209. For recent examples of Cu-catalyzed amination reactions,
2. see: (a) Zhu, D.; Wang, R.; Mao, J.; Xu, L.; Wu, F.; Wan, B. J. Mol. Catal. A 2006, 256, 256-260.
3. (b) Yeh, V. S. C.; Wiedeman, P. E. Tetrahedron Lett. 2006, 47, 6011-6016.
4. (c) Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742-8743.
5. For a relevant review, see: Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439-2463 and references therein.
6. For a recent review, see: Espino, C. G.; Du Bois, J. Modern Rhodium-Catalyzed Organic Reactions; Wiley: New York, 2005; pp 379-416. For selected examples,
7. see: (a) Fructos, M. R.; Trofimenko, S.; Diaz-Requejo, M. M.; Perez, P. J. J. Am. Chem. Soc. 2006, 128, 11784-11791.
8. (b) Liang, C.; Robert-Peillard, F.; Fruit, C.; Muller, P.; Dodd, R. H.; Dauban, P. Angew. Chem., Int. Ed. 2006, 45, 4641-4644.
9. (c) Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am. Chem. Soc. 2004, 126, 15378-15379.
10. (d) He, L.; Chan, P. W. H.; Tsui, W.-M.; Yu, W.-Y.; Che, C.-M. Org. Lett. 2004, 6, 2405-2408.
11. (e) Espino, C. G.; Wehn, P. W.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936.
12. (f) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598-600.
13. (g) Yu, X.-Q.; Huang, J.-S.; Zhou, X.-G.; Che, C.-M. Org. Lett. 2000, 2, 2233-2236.
14. (h) Breslow, R.; Gellman, S. H. J. Am. Chem. Soc. 1983, 105, 6728-6729.
15. (a) Kalberer, E. W.; Whitfield, S. R.; Sanford, M. S. J. Mol. Catal. A 2006, 251, 108-113.
16. (b) Kalyani, D.; Sanford, M. S. Org. Lett. 2005, 7, 4149-4152.
17. (c) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542-9543.
18. (d) Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300-2301.
19. (e) Yoneyama, T.; Crabtree, R. H. J. Mol. Catal. A 1996, 108, 35-40.
20. (a) Kalyani, D.; Dick, A. R.; Anani, W. Q.; Sanford, M. S. Tetrahedron 2006, 62, 11483-11498.
21. (b) Kalyani, D.; Dick, A. R.; Anani, W. Q.; Sanford, M. S. Org. Lett.. 2006, 8, 2523-2526.
22. (c) Hull, K. L.; Anani, W. Q.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 7134-7135.
23. (d) Giri, R.; Chen, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 2112-2115.
24. (a) Deprez, N. R.; Kalyani, D.; Krause, A.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972-4973.
25. (b) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330-7331.
26. (c) Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046-4048.
27. For mechanistic investigations into these transformations, see: (a) Dick, A. R.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 12790-12791.
28. (b) Dick, A. R.; Kampf, J. W.; Sanford, M. S. Organometallics 2005, 24, 482-485.
29. For recent examples of the catalytic conversion of C-H bonds to C-N bonds, see the following. (a) Cu catalysis: Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790-6791.
30. (b) Cu catalysis: Uemura, T.; Imoto, S.; Chatani, N. Chem. Lett. 2006, 35, 842-843.
31. II/0 catalysis: Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560-14561.
32. 2 was reported: Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048-9049.
33. Mahy, J. P.; Battioni, P.; Bedi, G.; Mansuy, D.; Fisher, J.; Weiss, R.; Morgenstern-Badarau, I. Inorg. Chem. 1988, 27, 353-359.
34. These iminoiodinane reagents are commonly used in the metal-catalyzed aziridination of olefins. In addition, analogous reagents are believed to form in situ in the amination reactions discussed in ref 3. For a relevant review, see: Halfen, J. A. Curr. Org. Chem. 2005, 9, 657-669.
35. Bhawmick, R.; Biswas, H.; Bandyopadhyay, P. J. Organomet. Chem. 1995, 498, 81-83.
36. Purification of this compound required both a basic extractive workup and multiple chromatographic separations. Complex 3 appears to be unstable under both of these conditions, resulting in low isolated yields.
37. 2O liberated from the metal center. See the Supporting Information for full details.
38. (a) Bugarčić, Z., D.; Liehr, G.; van Eldik, R. Dalton Trans. 2002, 951-956.
39. (b) Peters, J. C.; Harkins, S. B.; Brown, S. D.; Day, M. W. Inorg. Chem. 2001, 40, 5083-5091.
40. Cockburn, B. N.; Howe, D. V.; Keating, B. F.; Johnson, B. F. G.; Lewis, J. J. Chem. Soc., Dalton Trans. 1973, 404-410.
41. 1H NMR in both the crude reaction mixture and partially purified samples (Rajput, J.; Moss, J. R.; Hutton, A. T.; Hendricks, D. T.; Arendse, C. E.; Imrie, C. J. Organomet. Chem. 2004, 689, 1553-1568). The origin of its formation is unclear at this time, but we believe it contributes significantly to the low yield.
42. (a) Kamaraj, K.; Bandyopadhyay, D. Organometallics 1999, 18, 438-446.
43. (b) Kamaraj, K.; Bandyopadhyay, D. J. Am. Chem. Soc. 1997, 119, 8099-8100.
44. (a) Valk, J.-M.; Boersma, J.; van Koten, G. Organometallics 1996, 15, 4366-4372.
45. (b) Alsters, P. L.; Teunissen, H. T.; Boersma, J.; Spek, A. L.; van Koten, G. Organometallics 1993, 12, 4691-4696.
46. (a) Alsters, P. L.; Engel, P. F.; Hogerheide, M. P.; Copijn, M.; Spek, A. L.; van Koten, G. Organometallics 1993, 12, 1831-1844.
47. (b) Lagunas, M.; Gossage, R. A.; Spek, A. L.; van Koten, G. Organometallics 1998, 17, 731-741.
48. (c) Fahey, D. R. J. Organomet. Chem. 1971, 27, 283-292.
49. II, see: (a) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 1232-1233.
50. (b) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 13944-13945.
51. II, see: (a) Widenhoefer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6504-6511.
52. (b) Widenhoefer, R. A.; Zhong, H. A.
53. Yamada, Y.; Yamamoto, T.; Okawara, M. Chem. Lett. 1975, 361-362.
54. Södergren, M. J.; Alonso, D. A.; Bedekar, A. V.; Andersson, P. G. Tetrahedron Lett. 1997, 38, 6897-6900.
55. Cope, A. C.; Siekman, R. W. J. Am. Chem. Soc. 1965, 87, 3272-3273.
56. Nonoyama, M.; Suzuki, K.; Yamasaki, K. Proc. Jpn. Acad. 1969, 45, 605-608.
57. Selbin, J.; Gutierrez, M. A. J. Organomet. Chem. 1983, 246, 95-104.
58. Holcomb, H. L.; Nakanishi, S.; Flood, T. C. Organometallics 1996, 15, 4228-4234.