Copper-catalyzed aerobic oxidative functionalization of an arene C-H bond: Evidence for an aryl-copper(III) intermediate

Journal of the American Chemical Society

Volumn 132, Issue 34, 2010, Pages 12068-12073

  King, Amanda E ^a   Huffman, Lauren M ^a   Casitas, Alicia ^b   Costas, Miquel ^b   Ribas, Xavi ^b   Stahl, Shannon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b UNIVERSITY OF GIRONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AEROBIC OXIDATIONS; AMIDATION; C-H BOND; CATALYTIC MECHANISMS; IN-SITU; MECHANISTIC PATHWAYS; METHOXYLATION; OXIDATION STATE; OXIDATIVE FUNCTIONALIZATION; SPECTROSCOPIC STUDIES; STOICHIOMETRIC OXIDANT;

CATALYSIS; SPECTROSCOPIC ANALYSIS;

CATALYTIC OXIDATION;

CARBON; COPPER; COPPER COMPLEX; HYDROGEN; ORGANOMETALLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON; SODIUM BROMIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CROSS COUPLING REACTION; CYCLIC POTENTIOMETRY; ELECTRON TRANSPORT; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

BENZENE DERIVATIVES; CATALYSIS; COPPER; HETEROCYCLIC COMPOUNDS; KINETICS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; OXYGEN; STEREOISOMERISM;

EID: 77956093212     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1045378     Document Type: Article

References (82)

1. For leading references, see the following and articles cited therein
2. Gampp, H. and Zuberbühler, A. D. Met. Ions Biol. Syst. 1981, 12, 133-189
3. Gamez, P., Aubel, P. G., Driessen, W. L., and Reedijk, J. Chem. Soc. Rev. 2001, 30, 376-385
4. Lewis, E. A. and Tolman, W. B. Chem. Rev. 2004, 114, 1047-1076
5. van der Vlugt, J. I. and Meyer, F. Top. Organomet. Chem. 2007, 22, 191-240
6. Richter, J. M., Whitefield, B. W., Maimone, T. J., Lin, D. W., Castroviejo, M. P., and Baran, P. S. J. Am. Chem. Soc. 2007, 129, 12857-12869
7. Punniyamurthy, T. and Rout, L. Coord. Chem. Rev. 2008, 252, 134-154
8. For representative recent examples, see
9. Li, X. L., Hewgley, J. B., Mulrooney, C. A., Yang, J. M., and Kozlowski, M. C. J. Org. Chem. 2003, 68, 5500-5511
10. Menini, L. and Gusevskaya, E. V. Chem. Commun. 2006, 209-211
11. Basle, O. and Li, C.-J. Green Chem. 2007, 9, 1047-1050
12. Li, Z., Bohle, D. S., and Li, C.-J. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 8928-8933
13. Li, C.-J. Acc. Chem. Res. 2009, 42, 335-344
14. Ban, I., Sudo, T., Taniguchi, T., and Itami, K. Org. Lett. 2008, 10, 3607-3609
15. Borduas, N. and Powell, D. A. J. Org. Chem. 2008, 73, 7822-7825
16. DeMartino, M. P., Chen, K., and Baran, P. S. J. Am. Chem. Soc. 2008, 130, 11546-11560
17. Hewgley, J. B., Stahl, S. S., and Kozlowski, M. C. J. Am. Chem. Soc. 2008, 130, 12232-12233
18. Yang, L., Lu, Z., and Stahl, S. S. Chem. Commun. 2009, 6460-6462
19. For examples of such mechanistic proposals, see refs 2b, 2d, 5a, and 5c.
20. Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2, 422-424
21. Hay, A. S. J. Org. Chem. 1962, 27, 3320-3321
22. Siemsen, P., Livingston, R. C., and Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632-2657
23. Chen, X., Hao, X.-S., Goodhue, C. E., and Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790-6791
24. Uemura, T., Imoto, S., and Chatani, N. Chem. Lett. 2006, 35, 842-843
25. Mizuhara, T., Inuki, S., Oishi, S., Fujii, N., and Ohno, H. Chem. Commun. 2009, 3413-3415
26. Wang, W., Luo, F., Zhang, S., and Cheng, J. J. Org. Chem. 2010, 75, 2415-2418
27. Brasche, G. and Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 1932-1934
28. Ueda, S. and Nagasawa, H. Angew. Chem., Int. Ed. 2008, 47, 6411-6413
29. Ueda, S. and Nagasawa, H. J. Org. Chem. 2009, 74, 4272
30. Hamada, T., Ye, X., and Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833-835
31. Gao, Y. X., Wang, G., Chen, L., Xu, P. X., Zhao, Y. F., Zhou, Y. B., and Han, L. B. J. Am. Chem. Soc. 2009, 131, 7956-7957
32. Do, H.-Q. and Daugulis, O. J. Am. Chem. Soc. 2009, 131, 17052-17053
33. Monguchi, D., Fujiwara, T., Furukawa, H., and Mori, A. Org. Lett. 2009, 11, 1607-1610
34. Wang, Q. and Schreiber, S. L. Org. Lett. 2009, 11, 5178-5180
35. Fukuzawa, S., Shizimu, E., Atsuumi, Y., Haga, M., and Ogata, K. Tetrahedron Lett. 2009, 50, 2374-2376
36. Wie, Y., Zhao, H., Kann, J., Su, W., and Hong, M. J. Am. Chem. Soc. 2010, 132, 2522-2523
37. Chu, L. and Qing, F. L. J. Am. Chem. Soc. 2010, 132, 7262-7263
38. Matsuyama, N., Kitahara, M., Hirano, K., Satoh, T., and Miura, M. Org. Lett. 2010, 12, 2358-2361
39. Kitahara, M., Hirano, K., Tsurugi, H., Satoh, T., and Miura, M. Chem. - Eur. J. 2010, 16, 1772-1775
40. Li, Y., Jin, J., Qian, W., and Bao, W. Org. Biomol. Chem. 2010, 8, 326-330
41. Lyons, T. W. and Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169
42. 2 are also known. Representative examples are presented in the following review articles
43. Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420
44. Chen, X., Engle, K. M., Wang, D. H., and Yu, J. Q. Angew. Chem., Int. Ed. 2009, 48, 5094-5115
45. Sun, C.-L., Li, B.-J., and Shi, Z.-J. Chem. Commun. 2010, 46, 677-685
46. Furuta, H., Maeda, H., and Osuka, A. J. Am. Chem. Soc. 2000, 122, 803-807
47. Ribas, X., Jackson, D. A., Donnadieu, B., Mahía, J., Parella, T., Xifra, R., Hedman, B., Hodgson, K. O., Llobet, A., and Stack, T. D. P. Angew. Chem., Int. Ed. 2002, 41, 2991-2994
48. Maeda, H., Osuka, A., and Furuta, H. J. Am. Chem. Soc. 2003, 125, 15690-15691
49. Xifra, R., Ribas, X., Llobet, A., Poater, A., Duran, M., Solà, M., Stack, T. D. P., Benet-Buchholz, J., Donnadieu, B., Mahía, J., and Parella, T. Chem. - Eur. J. 2005, 11, 5146-5156
50. Pawlicki, M., Kańska, I., and Latos-GraZ̀yński, L. Inorg. Chem. 2007, 46, 6575-6584
51. Yao, B., Wang, D.-X., Huang, Z.-T., and Wang, M.-X. Chem. Commun. 2009, 2899-2901
52. Ribas, X., Calle, C., Poater, A., Casitas, A., Gómez, L., Xifra, R., Parella, T., Benet-Buchholz, J., Schweiger, A., Mitrikas, G., Sola, M., Llobet, A., and Stack, T. D. P. J. Am. Chem. Soc. 2010, DOI: 10.1021/ja101599e
53. Zuberbühler, A. D. Met. Ions Biol. Syst. 1976, 5, 325-368
54. See Supporting Information for further details.
55. Casitas, A., King, A. E., Parella, T., Costas, M., Stahl, S. S., and Ribas, X. Chem. Sci., DOI: 10.1039/C0SC00245C.
56. Huffman, L. M. and Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 9196-9197
57. II centers.
58. II accounts for 30-40% of the Cu at early stages of the reactions (t < 40 min).
59. III species.
60. A survey of mechanistic studies and proposals for the Glaser coupling reaction is presented in ref 4c. See also: Bohlmann, F., Schonowsky, H., Inhoffen, E., and Grau, G. Chem. Ber. 1964, 794-800
61. King, A. E., Brunold, T. C., and Stahl, S. S. J. Am. Chem. Soc. 2009, 131, 5044-5045
62. Chan, D. M. T., Monaco, K. L., Wang, R. P., and Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936
63. Evans, D. A., Katz, J. L., and West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940
64. Lam, P. Y. S., Clark, C. G., Saubern, S., Adams, J., Winters, M. P., Chan, D. M. T., and Combs, A. Tetrahedron Lett. 1998, 39, 2941-2944
65. Chan, D. M. T. and Lam, P. Y. S. In Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2005; pp 205 - 240.
66. Ley, S. V. and Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449
67. See refs 13, 20e, and the following additional leading references
68. Hassan, J., Sevignon, M., Gozzi, C., Schulz, E., and Lemaire, M. Chem. Rev. 2002, 102, 1359-1469
69. Beletskaya, I. P. and Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337-2364
70. Ma, D. and Cai, Q. Acc. Chem. Res. 2008, 41, 1450-1460
71. Monnier, F. and Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954-6971
72. Strieter, E. R., Bhayana, B., and Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 78-88
73. Tye, J. W., Weng, Z., Johns, A. M., Incarvito, C. D., and Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 9971-9983
74. Daugulis, O., Do, H. Q., and Shabashov, D. Acc. Chem. Res. 2009, 42, 1074-1086
75. Phipps, R. J. and Gaunt, M. J. Science 2009, 323, 1593-1597
76. Maiti, D., Sarjeant, A. A. N., Itoh, S., and Karlin, K. D. J. Am. Chem. Soc. 2008, 130, 5644-5645
77. Recently, a number of organocopper(III) intermediates have been characterized spectroscopically in nonoxidative Cu-mediated reactions, e.g., reactions of cuprates; see
78. Bertz, S. H., Cope, S., Murphy, M., Ogle, C. A., and Taylor, B. J. J. Am. Chem. Soc. 2007, 129, 7208-7209
79. Hu, H. and Snyder, J. P. J. Am. Chem. Soc. 2007, 129, 7210-7211
80. Bertz, S. H., Cope, S., Dorton, D., Murphy, M., and Ogle, C. A. Angew. Chem., Int. Ed. 2007, 46, 7082-7085
81. Gaertner, T., Henze, W., and Gschwind, R. M. J. Am. Chem. Soc. 2007, 129, 11362-11363
82. Jones, G. O., Liu, P., Houk, K. N., and Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 6205-6213