Allylic carbon-carbon double bond directed pd-catalyzed oxidative ortho -olefination of arenes

Journal of the American Chemical Society

Volumn 134, Issue 13, 2012, Pages 5738-5741

  Gandeepan, Parthasarathy ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

C-C DOUBLE BONDS; CARBON-CARBON DOUBLE BONDS; METALATIONS; OLEFINATION; ROOM TEMPERATURE; TERMINAL OXIDANTS;

AROMATIC COMPOUNDS;

CATALYSIS;

ALLYL COMPOUND; CARBON; ISOMERASE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; OLEFINATION; OXIDATION; ROOM TEMPERATURE;

EID: 84859371591     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja300168m     Document Type: Article

References (72)

1. Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731
2. Shilov, A. E.; Shulpin, G. B. Chem. Rev. 1997, 97, 2879
3. Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507
4. Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826
5. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
6. Giri, R.; Shi, B.-F.; Engle, K. M.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242
7. Zhang, M. Adv. Synth. Catal. 2009, 351, 2243
8. McMurray, L.; OHara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885
9. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976
10. Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633
11. Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318
12. Moritani, I.; Fujiwara, Y. Tetrahedron Lett. 1967, 8, 1119
13. Fujiwara, Y.; Moritani, I.; Danno, S.; Asano, R.; Teranishi, S. J. Am. Chem. Soc. 1969, 91, 7166
14. Fujiwara, Y.; Asano, R.; Moritani, I.; Teranishi, S. J. Org. Chem. 1976, 41, 1681
15. Fujiwara, Y.; Maruyama, O.; Yoshidomi, M.; Taniguchi, H. J. Org. Chem. 1981, 46, 851
16. Jia, C.; Lu, W.; Kitamura, T.; Fujiwara, Y. Org. Lett. 1999, 1, 2097
17. Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992
18. Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578
19. Cho, S. H.; Hwang, S. J.; Chang, S. J. Am. Chem. Soc. 2008, 130, 9254
20. Wu, J.; Cui, X.; Chen, L.; Jiang, G.; Wu, Y. J. Am. Chem. Soc. 2009, 131, 13888
21. Zhang, X.; Fan, S.; He, C.-Y.; Wan, X.; Min, Q.-Q.; Yang, J.; Jiang, Z.-X. J. Am. Chem. Soc. 2010, 132, 4506
22. Bras, J. L.; Muzart, J. Chem. Rev. 2011, 111, 1170
23. Heck, R. F. Acc. Chem. Res. 1979, 12, 146
24. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009
25. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442
26. Yu, J.-Q.; Giri, R.; Chen, X. Org. Biomol. Chem. 2006, 4, 4041
27. Daugulis, O.; Zaitzev, V. G.; Shabashov, D.; Pham, Q.-N.; Lazareva, A. Synlett 2006, 3382
28. Li, B.-J.; Yang, S.-D.; Shi, Z.-J. Synlett 2008, 949
29. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
30. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
31. Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654
32. Ashenhurst, J. A. Chem. Soc. Rev. 2010, 39, 540
33. Ackermann, L. Chem. Rev. 2011, 111, 1315
34. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780
35. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
36. Rousseau, G.; Breit, B. Angew. Chem., Int. Ed. 2011, 50, 2450
37. Shi, B.-F.; Zhang, Y.-H.; Lam, J. K.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 460
38. Wang, D.-H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315
39. Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 5072
40. Parthasarathy, K.; Jeganmohan, M.; Cheng, C.-H. Org. Lett. 2008, 10, 325
41. Thirunavukkarasu, V. S.; Parthasarathy, K.; Cheng, C.-H. Angew. Chem., Int. Ed. 2008, 47, 9462
42. Thirunavukkarasu, V. S.; Parthasarathy, K.; Cheng, C.-H. Chem.-Eur. J. 2010, 16, 1436
43. Gandeepan, P.; Parthasarathy, K.; Cheng, C.-H. J. Am. Chem. Soc. 2010, 132, 8569
44. Muralirajan, K.; Parthasarathy, K.; Cheng, C.-H. Angew. Chem., Int. Ed. 2011, 50, 4169
45. Karthikeyan, J.; Cheng, C.-H. Angew. Chem., Int. Ed. 2011, 50, 9880
46. Dawans, F. Tetrahedron Lett. 1971, 12, 1943
47. Tsuchimoto, T.; Kamiyama, S.; Negoro, R.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2003, 852
48. Wang, C.-C.; Lin, P.-S.; Cheng, C.-H. Tetrahedron Lett. 2004, 45, 6203
49. Yi, C.-Y.; Hua, R.-M.; Zeng, H.-X. Catal. Commun. 2008, 9, 85
50. Ma, H.; Sun, Q.; Li, W.; Wang, J.; Zhang, Z.; Yang, Y.; Lei, Z. Tetrahedron Lett. 2011, 52, 1569
51. Kiyooka, S.-i.; Takeshita, Y. Tetrahedron Lett. 2005, 46, 4279
52. Yamada, S.; Obora, Y.; Sakaguchi, S.; Ishii, Y. Bull. Chem. Soc. Jpn. 2007, 80, 1194
53. Tobisu, M.; Hyodo, I.; Onoe, M.; Chatani, N. Chem. Commun. 2008, 6013
54. Ryabov, A. D. Chem. Rev. 1990, 90, 403
55. Davidson, J. M.; Triggs, C. J. Chem. Soc. A 1968, 1324
56. Seregin, I. V.; Ryabova, V.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 7742
57. Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050
58. Chiong, H. A.; Daugulis, O. Org. Lett. 2007, 9, 1449
59. Li, R.; Liang, L.; Lu, W. Organometallics 2006, 25, 5973
60. Jones, W. D.; Feher, F. J. Acc. Chem. Res. 1989, 22, 91
61. Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1999, 121, 6616
62. Jia, C.; Lu, W.; Oyamada, J.; Kitamura, T.; Matsuda, K.; Irie, M.; Fujiwara, Y. J. Am. Chem. Soc. 2000, 122, 7252
63. Jia, C.; Piao, D.; Kitamura, T.; Fujiwara, Y. J. Org. Chem. 2000, 65, 7516
64. Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578
65. Delcamp, J. H.; White, M. C. J. Am. Chem. Soc. 2006, 128, 15076
66. Young, A. J.; White, M. C. J. Am. Chem. Soc. 2008, 130, 14090
67. Shi, Z.; Zhang, C.; Li, S.; Pan, D.; Ding, S.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 4572
68. Shi, Z.; Cui, Y.; Jiao, N. Org. Lett. 2010, 12, 2908
69. Bueno, A. C.; de Souza, A. O.; Gusevskaya, E. V. Adv. Synth. Catal. 2009, 351, 2491
70. Liégault, B.; Lee, D.; Huestis, M. P.; Stuart, D. R.; Fagnou, K. J. Org. Chem. 2008, 73, 5022
71. Liu, C. H.; Li, C. S.; Cheng, C. H. Organometallics 1994, 13, 18
72. Li, C. S.; Cheng, C. H.; Liao, F. L.; Wang, S. L. J. Chem. Soc., Chem. Commun. 1991, 10, 710