Pyridinyl directed alkenylation with olefins via Rh(III)-catalyzed C-C bond cleavage of secondary arylmethanols

Journal of the American Chemical Society

Volumn 133, Issue 39, 2011, Pages 15244-15247

  Li, Hu ^a   Li, Yang ^a   Zhang, Xi Sha ^a   Chen, Kang ^a   Wang, Xin ^a   Shi, Zhang Jie ^a,b  

^a PEKING UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

C-C BOND ACTIVATION; C-C BONDS; NEW STRATEGY; SECONDARY ALCOHOLS;

ALKENYLATION; CATALYSIS; RHODIUM;

OLEFINS;

ALKENE; RHODIUM;

ALKENYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 80053314804     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja205228y     Document Type: Article

References (75)

1. Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870
2. Murakami, M.; Ito, Y. Top. Organomet. Chem. 1999, 3, 97
3. van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759
4. Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610
5. Satoh, T.; Miura, M. Top. Organomet. Chem. 2005, 14, 1
6. Jun, C.-H.; Park, J.-W. Top. Organomet. Chem. 2007, 24, 117
7. Necas, D.; Kotora, M. Curr. Org. Chem. 2007, 11, 1566
8. Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 9307
9. Kim, S.; Takeuchi, D.; Osakada, K. J. Am. Chem. Soc. 2002, 124, 762
10. Kondo, T.; Kaneko, Y.; Taguchi, Y.; Nakamura, A.; Okada, T.; Shiotsuki, M.; Ura, Y.; Wada, K.; Mitsudo, T. J. Am. Chem. Soc. 2002, 124, 6824
11. Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Simhai, N.; Iverson, C. N.; Muller, C.; Satoh, T.; Jones, W. D. J. Mol. Catal. A: Chem. 2002, 189, 157
12. Bart, S. C.; Chirik, P. J. J. Am. Chem. Soc. 2003, 125, 886
13. Matsumura, S.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2003, 125, 8862
14. Ohmura, T.; Taniguchi, H.; Kondo, Y.; Suginome, M. J. Am. Chem. Soc. 2007, 129, 3518
15. Matsuda, T.; Shigeno, M.; Murakami, M. J. Am. Chem. Soc. 2007, 129, 12086
16. Winter, C.; Krause, N. Angew. Chem., Int. Ed. 2009, 48, 2460
17. Seiser, T.; Roth, O. A.; Cramer, N. Angew. Chem., Int. Ed. 2009, 48, 6320
18. Seiser, T.; Cramer, N. J. Am. Chem. Soc. 2010, 132, 5340
19. Seiser, T.; Cramer, N. Chem.-Eur. J. 2010, 16, 3383
20. Suggs, J. W.; Jun, C. H. J. Am. Chem. Soc. 1984, 106, 3054
21. Liou, S.-Y.; van der Boom, M. E.; Milstein, D. Chem. Commun. 1998, 687
22. Jun, C.-H.; Lee, H. J. Am. Chem. Soc. 1999, 121, 880
23. Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1999, 121, 8645
24. Jun, C.-H.; Lee, D.-Y.; Lee, H.; Hong, J.-B. Angew. Chem., Int. Ed. 2000, 39, 3070
25. Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem.-Eur. J. 2002, 8, 2422
26. Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222
27. Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 6646
28. Goossen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662
29. Tobisu, M.; Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2006, 128, 8152
30. Gunay, A.; Jones, W. D. J. Am. Chem. Soc. 2007, 129, 8729
31. Horino, Y. Angew. Chem., Int. Ed. 2007, 46, 2144
32. Takahashi, T.; Song, Z.; Hsieh, Y.-F.; Nakajima, K.; Kanno, K. J. Am. Chem. Soc. 2008, 130, 15236
33. Voutchkova, A.; Coplin, A.; Leadbeater, N. E.; Crabtree, R. H. Chem. Commun. 2008, 6312
34. Wang, C.; Piel, I.; Glorius, F. J. Am. Chem. Soc. 2009, 131, 4194
35. Najera, C.; Sansano, J. M. Angew. Chem., Int. Ed. 2009, 48, 2452
36. Sugiishi, T.; Kimura, A.; Nakamura, H. J. Am. Chem. Soc. 2010, 132, 5332
37. He, C.; Guo, S.; Huang, L.; Lei, A. J. Am. Chem. Soc. 2010, 132, 8273
38. Wang, C.; Rakshit, S.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 14006
39. Kondo, T.; Kodoi, K.; Nishinaga, E.; Okada, T.; Morisaki, Y.; Watanabe, Y.; Mitsudo, T. J. Am. Chem. Soc. 1998, 120, 5587
40. Terao, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2001, 123, 10407
41. Nishimura, T.; Araki, H.; Maeda, Y.; Uemura, S. Org. Lett. 2003, 5, 2997
42. Takada, Y.; Hayashi, S.; Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2006, 8, 2515
43. Niwa, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2007, 46, 2643
44. Shintani, R.; Takatsu, K.; Hayashi, T. Org. Lett. 2008, 10, 1191
45. Suehiro, T.; Niwa, T.; Yorimitsu, H.; Oshima, K. Chem.-Asian J. 2009, 4, 1217
46. Sai, M.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2011, 50, 3294
47. Zhao, P.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 3124
48. Zhao, P.; Hartwig, J. F. Organometallics 2008, 27, 4749
49. There is only one report of Rh-catalyzed C-C bond cleavage of secondary alcohols via H-transfer and consecutive C-C bond activation by Rh(I) catalysis rather than direct β-C elimination. Here, 2-amino-3-picoline is essential to promote the chelation-assisted strategy: Jun, C.-H.; Lee, D.-Y.; Kim, Y.-H.; Lee, H. Organometallics 2001, 20, 2928
50. Takezawa, E.; Sakaguchi, S.; Ishii, Y. Org. Lett. 1999, 1, 713
51. Han, C.; Uemura, D. Tetrahedron Lett. 2008, 49, 6988
52. Wang, A.; Jiang, H. J. Org. Chem. 2010, 75, 2321
53. Kimura, M.; Mori, M.; Tamaru, Y. Chem. Commun. 2007, 4504
54. Chiba, S.; Xu, Y.-J.; Wang, Y.-F. J. Am. Chem. Soc. 2009, 131, 12886
55. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1984.
56. Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph Series; American Chemical Society: Washington, DC, 1990.
57. Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. Science 1996, 274, 2044
58. Sheldon, R. A.; Arends, I. W. C. E.; ten Brink, G.-J.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774
59. Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221
60. Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185
61. Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620
62. Noyori, R.; Aoki, M.; Sato, K. Chem. Commun. 2003, 1977
63. Fujita, K.; Tanino, N.; Yamaguchi, R. Org. Lett. 2007, 9, 109 and references therein
64. Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169
65. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
66. Matsuura, Y.; Tamura, M.; Kochi, T.; Sato, M.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2007, 129, 9858
67. Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7094
68. Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908
69. Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9982
70. Shuai, Q.; Yang, L.; Guo, X.; Basle, O.; Li, C.-J. J. Am. Chem. Soc. 2010, 132, 12212
71. Tsai, A. S.; Tauchert, M. E.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2011, 133, 1248
72. Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350
73. Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449
74. Patureau, F. W.; Besset, T.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1064
75. Li, Y.; Li, B.-J.; Wang, W.-H.; Huang, W.-P.; Zhang, X.-S.; Chen, K.; Shi, Z.-J. Angew. Chem., Int. Ed. 2011, 50, 2115 and references therein