Copper-catalyzed amination of arylboronates with N,N-dialkylhydroxylamines

Angewandte Chemie - International Edition

Volumn 51, Issue 15, 2012, Pages 3642-3645

  Matsuda, Naoki ^a   Hirano, Koji ^a   Satoh, Tetsuya ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

amination; anilines; boron; copper; synthetic methods

Indexed keywords

ARYL AMINES; ARYLBORONATES; SYNTHETIC METHODS; UMPOLUNG;

AMINATION; ANILINE; BENZENE; BENZENE REFINING; BORON; CATALYSIS; COPPER; FUNCTIONAL GROUPS;

AMINES;

ANILINE DERIVATIVE; BORONIC ACID DERIVATIVE; COPPER; HYDROXYLAMINE;

AMINATION; ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

AMINATION; ANILINE COMPOUNDS; BORONIC ACIDS; CATALYSIS; COPPER; HYDROXYLAMINES;

EID: 84859550812     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201108773     Document Type: Article

References (63)

1. R. Hili, A. K. Yudin, Nat. Chem. Biol. 2006, 2, 284
2. Amino Group Chemistry, From Synthesis to the Life Sciences (Ed.:, A. Ricci,), Wiley-VCH, Weinheim, 2007.
3. S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558
4. Angew. Chem. Int. Ed. 2003, 42, 5400
5. D. M. T. Chan, P. Y. S. Lam, in Boronic Acids (Ed.:, D. G. Hall,), Wiley-VCH, Weinheim, 2005, chap. 5, p. 205
6. J. X. Qiao, P. Y. S. Lam, Synthesis 2011, 829.
7. D. M. T. Chan, K. L. Monaco, R.-P. Wang, M. P. Winters, Tetrahedron Lett. 1998, 39, 2933
8. P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; around the same time, Evans reported a relevant C-O bond-forming reaction
9. D. A. Evans, J. L. Katz, T. R. West, Tetrahedron Lett. 1998, 39, 2937.
10. J. C. Antilla, S. L. Buchwald, Org. Lett. 2001, 3, 2077
11. A. P. Combs, S. Tadesse, M. Rafalski, T. S. Haque, P. Y. S. Lam, J. Comb. Chem. 2002, 4, 179
12. X.-Q. Yu, Y. Yamamoto, N. Miyaura, Chem. Asian J. 2008, 3, 1517.
13. S. Liu, Y. Yu, L. S. Liebeskind, Org. Lett. 2007, 9, 1947
14. S. Liu, L. S. Liebeskind, J. Am. Chem. Soc. 2008, 130, 6918
15. Z. Zhang, Y. Yu, L. S. Liebeskind, Org. Lett. 2008, 10, 3005.
16. C. He, C. Chen, J. Cheng, C. Liu, W. Liu, Q. Li, A. Lei, Angew. Chem. 2008, 120, 6514
17. Angew. Chem. Int. Ed. 2008, 47, 6414.
18. H.-Y. Thu, W.-Y. Yu, C.-M. Che, J. Am. Chem. Soc. 2006, 128, 9048
19. A. A. Jordan-Hore, C. C. C. Johansson, M. Gulias, E. M. Beck, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 16184
20. T.-S. Mei, X. Wang, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 10806
21. B. Xiao, T.-J. Gong, J. Xu, Z.-J. Liu, L. Liu, J. Am. Chem. Soc. 2011, 133, 1466.
22. H. Tsutsui, Y. Hayashi, K. Narasaka, Chem. Lett. 1997, 317
23. M. J. Campbell, J. S. Johnson, Org. Lett. 2007, 9, 1521
24. T. Hatakeyama, Y. Yoshimoto, S. K. Ghorai, M. Nakamura, Org. Lett. 2010, 12, 1516; Zinc
25. A. M. Berman, J. S. Johnson, J. Am. Chem. Soc. 2004, 126, 5680
26. A. M. Berman, J. S. Johnson, Synlett 2005, 1799
27. A. M. Berman, J. S. Johnson, J. Org. Chem. 2006, 71, 219
28. T. J. Barker, E. R. Jarvo, J. Am. Chem. Soc. 2009, 131, 15598; Titanium
29. T. J. Barker, E. R. Jarvo, Angew. Chem. 2011, 123, 8475
30. Angew. Chem. Int. Ed. 2011, 50, 8325; also see
31. E. Erdik, M. Ay, Chem. Rev. 1989, 89, 1947
32. T. J. Barker, E. R. Jarbo, Synthesis 2011, 3954.
33. S. Jaime-Figueroa, Y. Liu, J. M. Muchowski, D. G. Putman, Tetrahedron Lett. 1998, 39, 1313
34. V. Cadierno, S. E. García-Garrido, J. Gimeno, N. Nebra, Chem. Commun. 2005, 4086
35. J.-Y. Wang, D.-X. Wang, Q.-Y. Zheng, Z.-T. Huang, M.-X. Wang, J. Org. Chem. 2007, 72, 2040.
36. T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 390
37. J. M. Murphy, X. Liao, J. F. Hartwig, J. Am. Chem. Soc. 2007, 129, 15434.
38. T. Ishiyama, H. Isou, T. Kikuchi, N. Miyaura, Chem. Commun. 2010, 46, 159.
39. C. S. Guy, T. C. Jones, Synlett 2009, 2253
40. A. S. Voisin, A. Bouillon, J.-C. Lancelot, A. Lesnard, S. Rault, Tetrahedron 2006, 62, 5350
41. C. C. Tzschucke, J. M. Murphy, J. F. Hartwig, Org. Lett. 2007, 9, 761.
42. T. Tsuda, T. Yazawa, K. Watanabe, T. Fujii, T. Saegusa, J. Org. Chem. 1981, 46, 192
43. P. Leoni, M. Pasquali, C. A. Ghilardi, J. Chem. Soc. Chem. Commun. 1983, 240
44. E. M. Meyer, S. Gambarotta, C. Floriani, A. Chiesi-Villa, C. Guastini, Organometallics 1989, 8, 1067.
45. M. Noack, R. Göttlich, Chem. Commun. 2002, 536; also see
46. T. Tsuritani, H. Shinokubo, K. Oshima, Org. Lett. 2001, 3, 2709
47. T. Tsuritani, H. Shinokubo, K. Oshima, J. Org. Chem. 2003, 68, 3246.
48. H. Ohmiya, N. Yokokawa, M. Sawamura, Org. Lett. 2010, 12, 2438
49. R. Shintani, K. Takatsu, T. Hayashi, Chem. Commun. 2010, 46, 6822
50. C.-T. Yang, Z.-Q. Zhang, Y.-C. Liu, L. Liu, Angew. Chem. 2011, 123, 3990
51. Angew. Chem. Int. Ed. 2011, 50, 3904
52. K. Takatsu, R. Shintani, T. Hayashi, Angew. Chem. 2011, 123, 5662
53. Angew. Chem. Int. Ed. 2011, 50, 5548
54. R. Shintani, K. Takatsu, T. Hayashi, Angew. Chem. 2011, 123, 8815
55. Angew. Chem. Int. Ed. 2011, 50, 8656
56. F. Yang, Z. Xu, Z. Wang, Z. Yu, R. Wang, Chem. Eur. J. 2011, 17, 6321.
57. J. K. Kochi, Organometallic Mechanisms and Catalysis, Academic Press, New York, 1978, p. 372
58. J. M. Klunder, G. H. Posner, Comprehensive Organic Synthesis, Vol. 3 (Eds.:, B. M. Trost, I. Fleming,), Pergamon, Oxford, 1991, 207
59. J.-E. Bäckvall, E. S. M. Persson, A. Bombrun, J. Org. Chem. 1994, 59, 4126
60. E. Nakamura, S. Mori, K. Morokuma, J. Am. Chem. Soc. 1998, 120, 8273
61. E. R. Bartholomew, S. H. Bertz, S. Cope, M. Murphy, C. A. Ogle, J. Am. Chem. Soc. 2008, 130, 11244.
62. 2 (2 b) was exposed to a THF solution of 1.0 equiv of CuOtBu, which was freshly generated from MesCu (5) and tBuOH. However, no reaction took place, and 2 b was quantitatively recovered intact (see below). Thus, our postulated reaction order (transmetalation then interaction with hydroxylamines) could be more plausible., P. O. Oguadinma, F. Schaper, Can. J. Chem. 2010, 88, 472.
63. N. Matsuda, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2011, 13, 3076.