Oxidative alkenylation/annulation of benzimidates via ruthenium(II)-catalyzed C-H activation to generate 3-methyleneisoindolin-1-ones

Advanced Synthesis and Catalysis

Volumn 357, Issue 2-3, 2015, Pages 395-399

  Li, Xing Guang ^a   Sun, Min ^a   Liu, Kai ^a   Liu, Pei Nian ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Alkenes; Annulation; C H activation; Cascade reaction; Ruthenium

Indexed keywords

EID: 84922670760     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201400727     Document Type: Article

References (75)

1. a) T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212-11222;
2. b) G. Y. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651-3678;
3. c) Z. Shi, C. Zhang, C. Tang, N. Jiao, Chem. Soc. Rev. 2012, 41, 3381-3430;
4. d) B. A. Perica, B. Christian, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879-5918;
5. e) S. I. Kozhushkov, L. Ackermann, Chem. Sci. 2013, 4, 886-896.
6. a) I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173-1193;
7. b) P. Thansandote, M. Lautens, Chem. Eur. J. 2009, 15, 5874-5883;
8. c) X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196-5217;
9. Angew. Chem. Int. Ed. 2009, 48, 5094-5115;
10. d) D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624-655;
11. e) T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147-1169;
12. f) J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. 2012, 124, 9092-9142;
13. Angew. Chem. Int. Ed. 2012, 51, 8960-9009.
14. a) M. Wasa, K. M. Engle, J-.Q. Yu, J. Am. Chem. Soc. 2010, 132, 3680-3681;
15. b) F. Wang, G. Song, X. Li, Org. Lett. 2010, 12, 5430-5433;
16. c) L. Ackermann, L. Wang, R. Wolfram, A. V. Lygin, Org. Lett. 2012, 14, 728-731;
17. d) C. Zhu, J. R. Falck, Chem. Commun. 2012, 48, 1674-1676;
18. e) S. Han, Y. Shin, S. Sharma, N. K. Mishra, J. Park, M. Kim, M. Kim, J. Jang, I. S. Kim, Org. Lett. 2014, 16, 2494-2497.
19. a) M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art, M. Nomura, J. Org. Chem. 1998, 63, 5211-5215;
20. b) K. Ueura, T. Satoh, M. Miura, Org. Lett. 2007, 9, 1407-1409;
21. c) S. Mochida, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, 74, 6295-6298;
22. d) L. Ackermann, J. Pospech, Org. Lett. 2011, 13, 4153-4155.
23. a) Y. Lu, D.-H. Wang, K. M. Engle, J-.Q. Yu, J. Am. Chem. Soc. 2010, 132, 5916-5921;
24. b) S. Nakanowatari, L. Ackermann, Chem. Eur. J. 2014, 20, 5409-5413.
25. N. K. Mishra, J. Park, S. Sharma, S. Han, M. Kim, Y. Shin, J. Jang, J. H. Kwak, Y. H. Jung, I. S. Kim, Chem. Commun. 2014, 50, 2350-2352.
26. J. Li, M. John, L. Ackermann, Chem. Eur. J. 2014, 20, 5403-5408.
27. V. P. Mehta, J.-A. García-López, M. F. Greaney, Angew. Chem. 2014, 126, 1555-1559;
28. Angew. Chem. Int. Ed. 2014, 53, 1529-1533.
29. D.-G. Yu, M. Suri, F. Glorius, J. Am. Chem. Soc. 2013, 135, 8802-8805.
30. a) G. Blaskó, D. J. Gula, M. Shamma, J. Nat. Prod. 1982, 45, 105-122;
31. b) Y.-C. Chia, F.-R. Chang, C.-M. Teng, Y.-C. Wu, J. Nat. Prod. 2000, 63, 1160-1163;
32. c) V. Fajardo, V. Elango, B. K. Cassels, M. Shamma, Tetrahedron Lett. 1982, 23, 39-42;
33. d) E. Valencia, J. Freyer, M. Shamma, V. Fajardo, Tetrahedron Lett. 1984, 25, 599-602;
34. e) E. Valencia, I. Weiss, S. Firdous, A. J. Freyer, M. Shamma, A. Urzffls, V. Fajardo, Tetrahedron 1984, 40, 3957-3962;
35. f) Y. Kato, H. Ebiike, K. Achiwa, N. Ashizawa, T. Kurihara, F. Kobayashi, Chem. Pharm. Bull. 1990, 38, 2060-2062;
36. g) Y. Kato, M. Takemoto, K. Achiwa, Chem. Pharm. Bull. 1993, 41, 2003-2006;
37. h) D. L. Comins, S. Schilling, Y. C. Zhang, Org. Lett. 2005, 7, 95-98;
38. i) N. Kanamitsu, T. Osaki, Y. Itsuji, M. Yoshimura, H. Tsujimoto, M. Soga, Chem. Pharm. Bull. 2007, 55, 1682-1688.
39. J.-M. Ferland, C. A. Demerson, L. G. Humber, Can. J. Chem. 1985, 63, 361-365.
40. M. H. Norman, D. J. Minick, G. C. Rigdon, J. Med. Chem. 1996, 39, 149-157.
41. Laboratori Baldacci S.p.A., Japanese Patent JP 59046268, 1984 ;
42. Chem. Abstr. 1984, 101, 54922.
43. B. Hulin, J. C. Parker, D. W. Piotrowski, U.S. Patent US2005234065, 2005.
44. W.LippmannU.S. Patent4,267,1891981
45. W. Lippmann, U.S. Patent 4,267,189, 1981 ; Chem. Abstr. 1981, 95, 61988m.
46. a) I. Pendrak, S. Barney, R. Wittrock, D. M. Lambert, W. D. Kingsbury, J. Org. Chem. 1994, 59, 2623-2625;
47. b) E. De Clercq, J. Med. Chem. 1995, 38, 2491-2517.
48. E. C. Taylor, P. Zhou, L. D. Jenning, Z. Mao, B. Hu, J.-G. Jun, Tetrahedron Lett. 1997, 38, 521-524.
49. a) W. Flitsch, H. Peters, Tetrahedron Lett. 1969, 10, 1161-1162;
50. b) P. Pigeon, B. Decroix, Tetrahedron Lett. 1996, 37, 7707-7710;
51. c) V. Rys, A. Couture, E. Deniau, P. Grandclaudon, Tetrahedron 2003, 59, 6615-6619;
52. d) A. Moreau, A. Couture, E. Deniau, P. Grandclaudon, J. Org. Chem. 2004, 69, 4527-4530;
53. e) T. Dominh, A. L. Johnson, J. E. Jones, P. P. Senise Jr, J. Org. Chem. 1977, 42, 4217-4221;
54. f) I. Takahashi, M. Hatanaka, Heterocycles 1997, 45, 2475-2499;
55. g) T. Yao, R. C. Larock, J. Org. Chem. 2005, 70, 1432-1437;
56. h) C. Koradin, W. Dohle, A. L. Rodriguez, B. Schmid, P. Knochel, Tetrahedron 2003, 59, 1571-1587;
57. )W.-D. Lu, C.-F. Lin, C.-J. Wang, S.-J. Wang, M.-J. Wu, Tetrahedron 2002, 58, 7315-7319;
58. j) G. Bianchi, M. Chiarini, F. Marinelli, L. Rossi, A. Arcadi, Adv. Synth. Catal. 2010, 352, 136-142;
59. k) C. Kanazawa, M. Terada, Chem. Asian J. 2009, 4, 1668-1672;
60. l) L. Li, M. Wang, X. Zhang, Y. Jiang, D. Ma, Org. Lett. 2009, 11, 1309-1312;
61. m) S. Couty, B. Lié-gault, C. Meyer, J. Cossy, Org. Lett. 2004, 6, 2511-2514;
62. n) H. Cao, L. McNamee, H. Alper, Org. Lett. 2008, 10, 5281-5284;
63. o) C. Sun, B. Xu, J. Org. Chem. 2008, 73, 7361-7364.
64. a) F. W. Patureau, T. Besset, F. Glorius, Angew. Chem. 2011, 123, 1096-1099;
65. Angew. Chem. Int. Ed. 2011, 50, 1064-1067;
66. b) X. Wei, F. Wang, G. Song, Z. Dub, X. Li, Org. Biomol. Chem. 2012, 10, 5521-5524;
67. c) J. Zhou, B. Li, Z.-C. Qian, B.-F. Shi, Adv. Synth. Catal. 2014, 356, 1038-1046;
68. d) Á. M. Martínez, N. Rodríguez, R. G. Array s, J. C. Carretero, Chem. Commun. 2014, 50, 6105-6107;
69. e) S. Cai, C. Chen, P. Shao, C. Xi, Org. Lett. 2014, 16, 3142-3145.
70. J. W. Wrigglesworth, B. Cox, G. C. Lloyd-Jones, K. I. Booker-Milburn, Org. Lett. 2011, 13, 5326-5329.
71. a) W. Hou, B. Zhou, Y. Yang, H. Feng, Y. Li, Org. Lett. 2013, 15, 1814-1817;
72. b) B. Zhou, W. Hou, Y. Yang, Y. Li, Chem. Eur. J. 2013, 19, 4701-4706.
73. J. Dong, F. Wang, J. You, Org. Lett. 2014, 16, 2884-2887.
74. M. C. Reddy, M. Jeganmohan, Org. Lett. 2014, 16, 4866-4869.
75. CCDC 1014386 contains the supplementary crystallographic data compound 3l in this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.