Ruthenium-catalyzed oxidative cross-coupling of chelating arenes and cycloalkanes

Angewandte Chemie - International Edition

Volumn 47, Issue 33, 2008, Pages 6278-6282

  Deng, Guojun ^a   Zhao, Liang ^b   Li, Chao Jun ^a  

^a MCGILL UNIVERSITY   (Canada)

^b Tulane University   (United States)

Author keywords

Alkanes; Arenes; C C coupling; C H activation; Ruthenium

Indexed keywords

AROMATIC COMPOUNDS; HYDROCARBONS; PARAFFINS;

ALKANES; ARENES; C-C COUPLING; C-H ACTIVATION;

RUTHENIUM;

EID: 53549084027     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801544     Document Type: Article

References (74)

1. P. T. Anastas, J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, New York, 1998.
2. For reviews on the reactions of C-H bonds, see: a) V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731;
3. b) G. Dyker, Angew. Chem. 1999, 111, 1808;
4. Angew. Chem. Int. Ed. 1999, 38, 1698;
5. c) T. Naota, H. Takaya, S. I. Murahashi, Chem. Rev. 1998, 98, 2599;
6. d) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174;
7. e) L. C. Campeau, D. R. Stuart, K. Fagnou, Aldrichimica Acta 2007, 40, 35;
8. f) K. Godula, D. Sames, Science 2006, 312, 67.
9. For recent examples, see: a) L. Ackermann, A. Althammer, R. Born, Angew. Chem. 2006, 118, 2681;
10. Angew. Chem. Int. Ed. 2006, 45, 2619;
11. b) C. Lenges, M. Brookhart, J. Am. Chem. Soc. 1999, 121, 6616;
12. c) F. Kakiuchi, S. Kan, K. Igi, N. Chatani, S. Murai, J. Am. Chem. Soc. 2003, 125, 1698;
13. d) Y. G. Lim, J. A. Ahn, C. H. Jun, Org. Lett. 2004, 6, 4687;
14. e) R. K. Thalji, J. A. Ellman, R. G. Bergman, J. Am. Chem. Soc. 2004, 126, 7192;
15. f) S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Nature 1993, 366, 529;
16. g) A. Lazareva, O. Daugulis, Org. Lett. 2006, 8, 5211;
17. h) M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2002, 124, 1586;
18. i) S. J. Tremont, H. ur Rahman, J. Am. Chem. Soc. 1984, 106, 5759;
19. j) V. G. Zaitsev, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 4156;
20. k) D. Kalyani, N. R. Deprez, L. V. Desai, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 7330;
21. l) A. R. Dick, K. L. Hull, M. S. Sanford, J. Am. Chem. Soc. 2004, 126, 2300;
22. m) R. Giri, X. Chen, J. Q. Yu, Angew. Chem. 2005, 117, 2150;
23. Angew. Chem. Int. Ed. 2005, 44, 2112;
24. n) R. Giri, J. Liang, J. G. Lei, J. J. Li, D. H. Wang, X. Chen, I. C. Naggar, C. Guo, B. M. Foxman, J. Q. Yu, Angew. Chem. 2005, 117, 7586;
25. Angew. Chem. Int. Ed. 2005, 44, 7420;
26. o) S. Yanagisawa, T. Sudo, R. Noyori, K. Itami, J. Am. Chem. Soc. 2006, 128, 11748;
27. p) S. I. Murahashi, N. Komiya, H. Terai, T. Nakae, J. Am. Chem. Soc. 2003, 125, 15312;
28. q) S. I. Murahashi, N, Komiya, H. Terai, Angew. Chem. 2005, 117, 7091;
29. Angew. Chem. Int. Ed. 2005, 44, 6931;
30. r) X. Chen, J. J. Li, X. S. Hao, C. E. Goodhue, J Q. Yu, J. Am. Chem. Soc. 2006, 128, 78;
31. s) X. Chen, C. E. Goodhue, J. Q. Yu, J. Am. Chem. Soc. 2006, 128, 12634;
32. t) R. Giri, N. Maugel, J. J. Li, D. H. Wang, S. P. Breazzano, L. B. Saunders, J. Q. Yu, J. Am. Chem. Soc. 2007, 129, 3510;
33. u) O. Daugulis, V. G. Zaitsev, Angew. Chem. 2005, 117, 4114;
34. Angew. Chem. Int. Ed. 2005, 44, 4046;
35. v) V. G. Zaitesv, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 13 154;
36. w) H. A. Chiong, O. Daugulis, Org. Lett. 2007, 9, 1449.
37. a) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2004, 126, 11810;
38. b) Z. Li, C.-J. Li, Org. Lett. 2004, 6, 4997;
39. c) Z. Li, C.-J. Li, Eur. J. Org. Chem. 2005, 3173;
40. d) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 6968-6969;
41. e) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 3672;
42. f) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2006, 128, 56;
43. g) Y. Zhang, C.-J. Li, J. Am. Chem. Soc. 2006, 128, 4242;
44. h) Y. Zhang, C.-J. Li, Angew. Chem. 2006, 118, 1983;
45. Angew. Chem. Int. Ed. 2006, 45, 1949;
46. i) O. Basle, C.-J. Li, Green Chem. 2007, 9, 1047;
47. j) Z. Li, D. S. Bohle, C.-J. Li, Proc. Natl. Acad. Sci. USA 2006, 103, 8928.
48. a) G. Cai, Y. Fu, Y. Li, X. Wan, Z.-J. Shi, J. Am. Chem. Soc. 2007, 129, 7666;
49. b) Z. Li, L. Cao, C.-J. Li, Angew. Chem. 2007, 119, 6625;
50. Angew. Chem. Int. Ed. 2007, 46, 6505.
51. a) L. Eberson, L. Gomez-Gonzalez, Acta Chem. Scand. 1973, 27, 1249;
52. b) H. Yoshimoto, H. Itatani, Bull. Chem. Soc. Jpn. 1973, 46, 2490;
53. c) K. Masui, H. Ikegami, A. Mori, J. Am. Chem. Soc. 2004, 126, 5074;
54. d) D. R. Stuart, K. Fagnou, Science 2007, 316, 1172;
55. e) D. R. Stuart, E. Villemure, K. Fagnou, J. Am. Chem. Soc. 2007, 129, 12072;
56. f) T. Dohi, M. Ito, K. Morimoto, M. Iwata, Y. Kita, Angew. Chem. Int. Ed. 2008, 47, 1301;
57. g) T. A. Dwight, N. R. Rue, D. Charyk, R. Josselyn, B. DeBoef, Org. Lett. 2007, 9, 3137;
58. h) B. Li, S. Tian, Z. Fang, Z. Shi, Angew. Chem. 2008, 120, 1131;
59. Angew. Chem. Int. Ed. 2008, 47, 1115;
60. i) K. L. Hull, M. S. Sanford, J. Am. Chem. Soc. 2007, 129, 11904;
61. j) J.-B. Xia, S.-L. You. Organometallics 2007, 26, 4869.
62. Y. Zhang, C.-J. Li, Eur. J. Org. Chem. 2007, 4654.
63. Y. Zhang, J. Feng, C.-J. Li, J. Am. Chem. Soc. 2008, 130, 2900.
64. For a review on the importance of the pyridine structure, see: G. D. Henry, Tetrahedron 2004, 60, 6043.
65. a) N. Chatani, Y. Ie, F. Kakiuchi, S. Murai, J. Org. Chem. 1997, 62, 2604;
66. b) Ruthenium Catalysts and Fine Chemistry (Eds.: C. Bruneau, P. Dixneuf), Spinger, Heidelberg, 2004;
67. c) I. Ozdemir, S. Demir, B. Cetinkaya, C. Gourlaouen, F. Maseras, C. Bruneau, P. H. Dixneuf, J. Am. Chem. Soc. 2008, 130, 1156.
68. a) D. T. Sawyer, A. Sobkowiak, T. Matsushita, Acc. Chem. Res. 1996, 29, 409;
69. b) C. Walling, Acc. Chem. Res. 1998, 31, 155;
70. c) D. H. R. Barton, D. Doller, Pure Appl. Chem. 1991, 63, 1567.
71. For isotope effects in C-H bond activation, see: a) J. A. Tunge, L. N. Foresee, Orgnometallics 2005, 24, 6440;
72. b) W. D. Jones, Acc. Chem. Res. 2003, 36, 140;
73. c) H. A. Zhong, J. A. Labinger, J. E. Bercaw, J. Am. Chem. Soc. 2002, 124, 1378;
74. d) W. D. Jones, F. J. Feher, Acc. Chem. Res. 1989, 22, 91.