CU-catalyzed cross-dehydrogenative coupling: A versatile strategy for C-C bond formations via the oxidative activation of sp3 C-H bonds

Proceedings of the National Academy of Sciences of the United States of America

Volumn 103, Issue 24, 2006, Pages 8928-8933

  Li, Zhiping ^a   Bohle, D Scott ^a   Li, Chao Jun ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

Baylis Hillman reaction; C H activation; Catalysis; Friedel Crafts reaction; Mannich reaction

Indexed keywords

COPPER; NITROGEN;

ALKYNYLATION; ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CATALYST; DEHYDROGENATION; FRIEDEL CRAFTS REACTION; HYDROGEN BOND; MANNICH REACTION; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

CARBON; COPPER; HYDROGEN; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; TETRAHYDROISOQUINOLINES;

EID: 33745157509     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0601687103     Document Type: Article

References (84)

1. De Meijere, A. & Diederich, F., eds. (2004) Metal-Catalyzed Cross-Coupling Reactions (Wiley-VCH, Weinheim, Germany), 2nd Ed.
2. Crabtree, R. H. (2004) J. Organomet. Chem. 689, 4083-4091.
3. Ritleng, V., Sirlin, C. & Pfeffer, M. (2002) Chem. Rev. 102, 1731-1770.
4. Jia, C., Kitamura, T. & Fujiwara, Y. (2001) Acc. Chem. Res. 34, 633-639.
5. Dyker, G. (1999) Angew. Chem. Int. Ed. 38, 1698-1712.
6. Shilov, A. E. & Shul'pin, G. B. (1997) Chem. Rev. 97, 2879-2932.
7. Murahashi, S.-I., Komiya, N., Terai, H. & Nakae, T. (2003) J. Am. Chem. Soc. 125, 15312-15313.
8. Doye, S. (2001) Angew. Chem. Int. Ed. 40, 3351-3353.
9. Chatani, N., Asaumi, T., Yorimitsu, S., Ikeda, T., Kakiuchi, F. & Murai, S. (2001) J. Am. Chem. Soc. 123, 10935-10941.
10. Chatani, N., Asaumi, T., Ikeda, T., Yorimitsu, S., Ishii, Y., Kakiuchi, F. & Murai, S. (2000) J. Am. Chem. Soc. 122, 12882-12883.
11. Jun, C.-H., Hwang, D.-C. & Na, S.-J. (1998) Chem. Commun. 1405-1406.
12. Sakaguchi, S., Kubo, T. & Ishii, Y. (2001) Angew. Chem. Int. Ed. 40, 2534-2536.
13. Sezen, B. & Sames, D. (2005) J. Am. Chem. Soc. 127, 5284-5285.
14. Sezen, B. & Sames, D. (2004) J. Am. Chem. Soc. 126, 13244-13246.
15. DeBoef, B., Pastine, S. J. & Sames, D. (2004) J. Am. Chem. Soc. 126, 6556-6557.
16. Davies, H. M. L. & Jin, Q. (2004) Org. Lett. 6, 1769-1772.
17. Davies, H. M. L., Venkataramani, C., Hansen, T. & Hopper, D. W. (2003) J. Am. Chem. Soc. 125, 6462-6468.
18. Yoshimitsu, T., Arano, Y. & Nagaoka, H. (2005) J. Am. Chem. Soc. 127, 11610-11611.
19. Maruyama, T., Suga, S. & Yoshida, J.-I. (2005) J. Am. Chem. Soc. 127, 7324-7325.
20. Suga, S., Nishida, T., Yamada, D., Nagaki, A. & Yoshida, J.-I. (2004) J. Am. Chem. Soc. 126, 14338-14339.
21. Suga, S., Suzuki, S. & Yoshida, J.-I. (2002) J. Am. Chem. Soc. 124, 30-31.
22. Yoshida, J.-I., Suga, S., Suzuki, S., Kinomura, N., Yamamoto, A. & Fujiwara, K. (1999) J. Am. Chem. Soc. 121, 9546-9549.
23. Yi, C. S., Yun, S. Y. & Guzei, I. A. (2004) Organometallics 23, 5392-5395.
24. Li, Z. & Li, C.-J. (2006) J. Am. Chem. Soc. 128, 56-57.
25. Li, Z. & Li, C.-J. (2005) Eur. J. Org. Chem. 3173-3176.
26. Li, Z. & Li, C.-J. (2005) J. Am. Chem. Soc. 127, 6968-6969.
27. Li, Z. & Li, C.-J. (2005) J. Am. Chem. Soc. 127, 3672-3673.
28. Li, Z. & Li, C.-J. (2004) Org. Lett. 6, 4997-4999.
29. Li, Z. & Li, C.-J. (2004) J. Am. Chem. Soc. 126, 11810-11811.
30. Lucet, D., Le Gall, T. & Mioskowski, C. (1998) Angew. Chem. Int. Ed. 37, 2580-2627.
31. Baer, H. H. & Urbas, L. (1970) in The Chemistry of the Nitro and Nitroso Group, ed. Fruer, H. (Interscience, New York), Part 2, pp. 75-200.
32. Bernardi, L., Bonini, B. F., Capito, E., Dessole, G., Comes-Franchini, M., Fochi, M. & Ricci, A. (2004) J. Org. Chem. 69, 8168-8171.
33. Adams, H., Anderson, J. C., Peace, S. & Pennell, A. M. K. (1998) J. Org. Chem. 63, 9932-9934.
34. Ballini, R. & Petrini, M. (2004) Tetrahedron 60, 1017-1047.
35. Breuer, E. & Melumad, D. (1973) J. Org. Chem. 38, 1601-1602.
36. Choudary, B. M. & Reddy, P. N. (1996) J. Mol. Cat. A Chem. 112, 385-388.
37. Kharasch, M. S. & Sosnovsky, G. (1958) Tetrahedron 3, 105-112.
38. Basavaiah, D., Rao, A. J. & Satyanarayana, T. (2003) Chem. Rev. 103, 811-892.
39. Jellerichs, B. G., Kong, J.-R. & Krische, M. J. (2003) J. Am. Chem. Soc. 125, 7758-7759.
40. Basavaiah, D., Sharada, D. S., Kumaragurubaran, N. & Reddy, R. M. (2002) J. Org. Chem. 67, 7135-7137.
41. Krafft, M. E. & Haxell, T. F. N. (2005) J. Am. Chem. Soc. 127, 10168-10169.
42. Krafft, M. E., Seibert, K. A., Haxell, T. F. N. & Hirosawa, C. (2005) Chem. Commun. 5772-5774.
43. Olah, G. A. (1963) Friedel-Crafts and Related Reactions (Wiley, New York).
44. Olah, G. A. (1973) Friedel-Crafts Chemistry (Wiley, New York).
45. Bandini, M., Melloni, A. & Umani-Ronchi, A. (2004) Angew. Chem. Int. Ed. 43, 550-556.
46. Luo, Y. & Li, C.-J. (2004) Chem. Commun. 1930-1931.
47. Jorgensen, K. A. (2003) Synthesis 1117-1125.
48. Ishii, A., Soloshonok, V. A. & Mikami, K. (2000) J. Org. Chem. 65, 1597-1599.
49. Johannsen, M. (1999) Chem. Commun. 2233-2234.
50. Olah, G. A., Khrisnamurti, R. & Prakash, G. K. S. (1991) in Comprehensive Organic Synthesis, eds. Trost, B. M. & Fleming, I. (Pergamon, New York), 1st Ed., Vol. 3, pp. 293-340.
51. Krasnov, K. A. & Kartsev, V. G. (2002) Russ. J. Org. Chem. 38, 430-436.
52. Ryan, R. P., Hamby, R. A. & Wu, Y.-H. (1975) J. Org. Chem. 40, 724-728.
53. Shirasaka, T., Takuma, Y., Shimpuku, T. & Imaki, N. (1990) J. Org. Chem. 55, 3767-6771.
54. Wang, X., Dong, Y., Sun, J., Xu, X., Li, R. & Hu, Y. (2005) J. Org. Chem. 70, 1897.
55. Cardellicchio, C., Ciccarella, G., Naso, F., Perna, F. & Tortorella, P. (1999) Tetrahedron 55, 14685-14692.
56. Ji, J.-X., Wu, J., Au-Yeung, T. T.-L., Yip, C.-W., Haynes, R. K. & Chan, A. S. C. (2005) J. Org. Chem. 70, 1093-1095.
57. Chen, Y., Yekta, S. & Yudin, A. K. (2003) Chem. Rev. 103, 3155-3212.
58. Nakamura, H., Kamakura, T., Ishikura, M. & Biellmann, J.-F. (2004) J. Am. Chem. Soc. 126, 5958-5959.
59. Murai, T., Mutoh, Y., Ohta, Y. & Murakami, M. (2004) J. Am. Chem. Soc. 126, 5968-5969.
60. Ahn, J. H., Joung, M. J., Yoon, N. M., Oniciu, D. C. & Katritzky, A. R. (1999) J. Org. Chem. 64, 488-492.
61. Wei, C. & Li, C.-J. (2002) Green Chem. 4, 39-41.
62. Fassler, R., Frantz, D. E., Oetiker, J. & Carreira, E. M. (2002) Angew. Chem. Int. Ed. 41, 3054-3056.
63. Fischer, C. & Carreira, E. M. (2001) Org. Lett. 3, 4319-4321.
64. Frantz, D. E., Fassler, R. & Carreira, E. M. (1999) J. Am. Chem. Soc. 121, 11245-11246.
65. Miura, M., Enna, M., Okuro, K. & Nomura, M. (1995) J. Org. Chem. 60, 4999-5004.
66. Wei, C., Mague, J. T. & Li, C.-J. (2004) Proc. Natl. Acad. Sci. USA 101, 5749-5754.
67. Koradin, C., Polborn, K. & Knochel, P. (2002) Angew. Chem. Int. Ed. 41, 2535-2538.
68. Zhang, J., Wei, C. & Li, C.-J. (2002) Tetrahedron Lett. 43, 5731-5733.
69. Wei, C. & Li, C.-J. (2003) J. Am. Chem. Soc. 125, 9584-9585.
70. Yao, X. & Li, C.-J. (2006) Org. Lett. 8, 1953-1955.
71. Wei, C. & Li, C.-J. (2005) Lett. Org. Chem. 2, 410-414.
72. Wei, C., Li, Z. & Li, C.-J. (2003) Org. Lett. 5, 4473-4475.
73. Yao, X. & Li, C.-J. (2005) Org. Lett. 7, 4395-4398.
74. Li, Z.; Wei, C., Chen, L., Varma, R. S. & Li, C.-J. (2004) Tetrahedron Lett. 45, 2443-2446.
75. Luo, Y., Li, Z. & Li, C.-J. (2005) Org. Lett. 7, 2675-2678.
76. Nicolaou, K. C., Mathison, C. J. N. & Montagnon, T. (2004) J. Am. Chem. Soc. 126, 5192-5201.
77. Wang, F. & Sayre, L. M. (1992) J. Am. Chem. Soc. 114, 248-255.
78. Leonard, N. J. & Leubner, G. W. (1949) J. Am. Chem. Soc. 71, 3408-3411.
79. Black, D. A. & Arndtsen, B. A. (2004) Org. Lett. 6, 1107-1110.
80. Murahashi, S.-I. (1995) Angew. Chem. Int. Ed. 34, 2443-2465.
81. Barton, D. H. R., Beviere, S. D., Chavasiri, W., Csuhai, E. & Doller, D. (1992) Tetrahedron 48, 2895-2910.
82. Kharasch, M. S. & Fono, A. (1959) J. Org. Chem. 24, 72-78.
83. Murahashi, S.-I., Naota, T., Kuwabara, T., Saito, T., Kumobayashi, H. & Akutagawa, S. (1990) J. Am. Chem. Soc. 112, 7820-7822.
84. Murahashi, S.-I., Naota, T. & Yonemura, K. (1988) J. Am. Chem. Soc. 110, 8256-8258.