N-amidation by copper-mediated cross-coupling of organostannanes or boronic acids with O-acetyl hydroxamic acids

Organic Letters

Volumn 10, Issue 14, 2008, Pages 3005-3008

  Zhang, Zhihui ^a   Yu, Ying ^a,b   Liebeskind, Lanny S ^a  

^a EMORY UNIVERSITY   (United States)

^b THERAVANCE INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; COPPER; HYDROXAMIC ACID; ORGANOTIN COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

BORONIC ACIDS; CATALYSIS; COPPER; HYDROXAMIC ACIDS; MOLECULAR STRUCTURE; ORGANOTIN COMPOUNDS;

EID: 52049112609     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8009682     Document Type: Article

References (44)

1. For some recent reviews, see: (a) Beletskaya, I. P Pure Appl. Chem. 2005, 77, 2021-2027.
2. (b) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337-2364.
3. (c) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
4. (a) Leading reviews: Buchwald, S. L.; Mauger, C.; Mignani, G.; Scholzc, U. Adv. Synth. Catal. 2006, 348, 23-39.
5. (b) Hartwig, J. F. Synlett 2006, 1283-1294.
6. (c) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131-209.
7. (d) Hartwig, J. F. Compr. Coord. Chem. II 2004, 9, 369-398.
8. (e) Schlummer, B.; Scholz, U. Adv. Synth. Catal. 2004, 346, 1599-1626.
9. For some examples, see: (a) Lam, P. Y. S.; Vincent, G.; Bonne, D.; Clark, C. G. Tetrahedron Lett. 2003, 44, 4927-4931.
10. (b) Chan, D. M. T.; Monaco, K. L.; Li, R.; Bonne, D.; Clark, C. G.; Lam, P. Y. S. Tetrahedron Lett. 2003, 44, 3863-3865.
11. (c) Lam, P. Y. S.; Bonne, D.; Vincent, G.; Clark, C. G.; Combs, A. P. Tetrahedron Lett. 2003, 44, 1691-1694.
12. (d) Lam, P. Y. S.; Deudon, S.; Hauptman, E.; Clark, C. G. Tetrahedron Lett. 2001, 42, 2427-2429.
13. (e) Evans, D. A; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940.
14. (a) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236.
15. (b) Collman, J. P.; Zhong, M.; Zeng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531.
16. (c) Collman, J. P.; Zhong, M.; Zhang, C.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
17. (d) Antilla, J. C.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079.
18. (e) Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 4397-4400.
19. (f) Bolshan, Y.; Batey, R. A. Angew. Chem., Int. Ed. 2008, 47, 2109-2112.
20. (a) Kitamura, M.; Suga, T.; Chiba, S.; Narasaka, K. Org. Lett. 2004, 6, 4619-4621.
21. (b) Narasaka, K. Pure Appl. Chem. 2002, 74, 143-149.
22. (c) Tsutsui, H.; Hayashi, Y.; Narasaka, K. Chem. Lett. 1997, 317-318.
23. (a) Campbell, M. J.; Johnson, J. S. Org. Lett. 2007, 9, 1521-1524.
24. (b) Berman, A. M.; Johnson, J. S. J. Org. Chem. 2006, 71, 219-224.
25. (c) Berman, A. M.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 5680-5681.
26. (a) Hydrazines and hydroxyamines are known to undergo Lam-like oxidative N- and O-arylation with boronic acids without cleavage of the heteroatom-heteroatom bond: Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142.
27. (b) Suzuki, H.; Yamamoto, A. J. Chem. Res., Synop. 1992, 8, 280-281.
28. (a) Liu, S.; Yu, Y.; Liebeskind, L. S. Org. Lett. 2007, 9, 1947-1950.
29. (b) See also Cu(I)-catalyzed couplings of boronic acids with nitrosoaromatics: Yu, Y.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2004, 6, 26312634>.
30. Liu, S.; Liebeskind, L. S. J. Am. Chem. Soc. 2008, 130, 6918-6919.
31. 4,and evaporated. The residue was then subjected to preparative plate silica chromatography using hexanes/EtOAc as eluent.
32. (a) Allred, G.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749.
33. (b) Wittenberg, R.; Srogl, J.; Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 3033-3035.
34. 4, and evaporated. The residue was then subjected to preparative plate silica chromatography using hexanes/EtOAc as eluent.
35. For oxidative addition of the N-O bond to various transition metals such as Re, Pd, and Cu, see: (a) Kusama, H.; Yamashita, Y.; Uchiyama, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 965-975.
36. (b) Ferreira, C. M. P.; Guedes da Silva, M. F. C.; Kukushkin, V. Y.; Fraústo da Silva, J. J. R.; Pombeiro, A. J. L. J. Chem. Soc., Dalton Trans. 1998, 32, 5-326.
37. (c) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45-46.
38. (d) Tsutsui, H.; Narasaka, K. Chem. Lett. 2001, 526-527.
39. (e) Kitamura, M.; Zaman, S.; Narasaka, K. Synlett 2001, 974-976.
40. (f) Kitamura, M; Narasaka, K. Chem. Rec. 2002, 2, 268-277.
41. (g) Chiba, S.; Kitamura, M.; Saku, O.; Narasaka, K. Bull. Chem. Soc. Jpn. 2004, 77, 785-796.
42. (h) Tsutsui, H.; Hayashi, Y.; Narasaka, K. Chem. Lett. 1997, 317-318.
43. (i) Narasaka, K. Pure Appl. Chem. 2002, 74, 143-149.
44. This reduction has been commonly found with various O-substituted hydroxamic acids, even with O-methyl hydroxamic acid. A Ti(III)-mediated reduction of O-methyl hydroxamic acid has been reported: Fisher, L. E.; Caroon, J. M.; Jahangir; Russell Stabler, J. S.; Lundberg, S.; Muchowski, J. M. J. Org. Chem. 1993, 58, 3643-3647.