Regiodivergent access to five- and six-membered benzo-fused lactams: Ru-catalyzed olefin hydrocarbamoylation

Journal of the American Chemical Society

Volumn 136, Issue 3, 2014, Pages 1125-1131

  Li, Bin ^a,b,c   Park, Yoonsu ^a,b   Chang, Sukbok ^a,b  

^a Institute for Basic Science   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^c NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SPECIES; CATALYTIC SYSTEM; COSOLVENTS; FORMAMIDES; HALIDE ADDITIVES; OXIDATIVE ADDITIONS; REACTION PATHWAYS; TRINUCLEAR COMPLEX;

AMIDES; CATALYSIS; OLEFINS;

CYCLIZATION;

ALKENE; DIMETHYL SULFOXIDE; HALIDE; LACTAM DERIVATIVE; TOLUENE;

ARTICLE; CARBAMOYLATION; CATALYSIS; CATALYST; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 84892969930     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja411913e     Document Type: Article

References (75)

1. Willis, M. C. Chem. Rev. 2010, 110, 725
2. Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222
3. Jun, C.-H.; Jo, E.-A.; Park, J.-W. Eur. J. Org. Chem. 2007, 1869
4. Leung, J. C.; Krische, M. J. Chem. Sci. 2012, 3, 2202
5. von Delius, M.; Le, C. M.; Dong, V. M. J. Am. Chem. Soc. 2012, 134, 15022
6. Chaplin, A. B.; Hooper, J. F.; Weller, A. S.; Willis, M. C. J. Am. Chem. Soc. 2012, 134, 4885
7. Murphy, S. K.; Coulter, M. M.; Dong, V. M. Chem. Sci. 2012, 3, 355
8. Piel, I.; Steinmetz, M.; Hirano, K.; Fröhlich, R.; Grimme, S.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 4983
9. Zhang, H.-J.; Bolm, C. Org. Lett. 2011, 13, 3900
10. Phan, D. H. T.; Kou, K. G. M.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 16354
11. Coulter, M. M.; Kou, K. G. M.; Galligan, B.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 16330
12. Pawley, R. J.; Moxham, G. L.; Dallanegra, R.; Chaplin, A. B.; Brayshaw, S. K.; Weller, A. S.; Willis, M. C. Organometallics 2010, 29, 1717
13. Hirano, K.; Biju, A. T.; Piel, I.; Glorius, F. J. Am. Chem. Soc. 2009, 131, 14190
14. Shibata, Y.; Tanaka, K. J. Am. Chem. Soc. 2009, 131, 12552
15. Sim, Y.-K.; Lee, H.; Park, J.-W.; Kim, D.-S.; Jun, C.-H. Chem. Commun. 2012, 48, 11787
16. Lenden, P.; Entwistle, D. A.; Willis, M. C. Angew. Chem., Int. Ed. 2011, 50, 10657
17. Parsons, S. R.; Hooper, J. F.; Willis, M. C. Org. Lett. 2011, 13, 998
18. González-Rodríguez, C.; Parsons, S. R.; Thompson, A. L.; Willis, M. C. Chem.-Eur. J. 2010, 16, 10950 and also see ref 2a
19. Khan, H. A.; Kou, K. G. M.; Dong, V. M. Chem. Sci. 2011, 2, 407
20. Phan, D. H. T.; Kim, B.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 15608 and references cited therein
21. Trost, B. M. Acc. Chem. Res. 2002, 35, 695
22. Trost, B. M. Science 1991, 254, 1471
23. Brennfuehrer, A.; Neumann, H.; Beller, M. ChemCatChem 2009, 1, 28
24. El Ali, B.; Alper, H. Hydrocarboxylation and hydroesterification reactions catalyzed by transition metal complexes. In Transition Metals for Organic Synthesis, 2 nd ed.; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004; pp 113-132. For selected examples, see
25. Konishi, H.; Ueda, T.; Muto, T.; Manabe, K. Org. Lett. 2012, 14, 4722
26. Katafuchi, Y.; Fujihara, T.; Iwai, T.; Terao, J.; Tsuji, Y. Adv. Synth. Catal. 2011, 353, 475
27. Park, E. J.; Lee, J. M.; Han, H.; Chang, S. Org. Lett. 2006, 8, 4355
28. Wang, L.; Floreancig, P. E. Org. Lett. 2004, 6, 4207
29. Ko, S.; Lee, C.; Choi, M.-G.; Na, Y.; Chang, S. J. Org. Chem. 2003, 68, 1607
30. Na, Y.; Ko, S.; Hwang, L. K.; Chang, S. Tetrahedron Lett. 2003, 44, 4475
31. Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750
32. Lugan, N.; Lavigne, G.; Soulié, J. M.; Fabre, S.; Kalck, P.; Saillard, J. Y.; Halet, J. F. Organometallics 1995, 14, 1712
33. Lavigne, G.; Lugan, N.; Kalck, P.; Soulié, J. M.; Lerouge, O.; Saillard, J. Y.; Halet, J. F. J. Am. Chem. Soc. 1992, 114, 10669
34. Armanino, N.; Carreira, E. M. J. Am. Chem. Soc. 2013, 135, 6814
35. Nath, D. C. D.; Fellows, C. M.; Kobayashi, T.; Hayashi, T. Aust. J. Chem. 2006, 59, 218
36. Ko, S.; Han, H.; Chang, S. Org. Lett. 2003, 5, 2687
37. Kondo, T.; Okada, T.; Mitsudo, T.-a. Organometallics 1999, 18, 4123
38. Tsuji, Y.; Yoshii, S.; Ohsumi, T.; Kondo, T.; Watanabe, Y. J. Organomet. Chem. 1987, 331, 379
39. Donets, P. A.; Cramer, N. J. Am. Chem. Soc. 2013, 135, 11772
40. Miyazaki, Y.; Yamada, Y.; Nakao, Y.; Hiyama, T. Chem. Lett. 2012, 41, 298
41. Nakao, Y.; Idei, H.; Kanyiva, K. S.; Hiyama, T. J. Am. Chem. Soc. 2009, 131, 5070
42. Mahatthananchai, J.; Dumas, A. M.; Bode, J. W. Angew. Chem., Int. Ed. 2012, 51, 10954
43. Yang, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2013, 135, 10642
44. Ding, Z.; Yoshikai, N. Angew. Chem., Int. Ed. 2013, 52, 8574
45. Shareef, A.-R.; Sherman, D. H.; Montgomery, J. Chem. Sci. 2012, 3, 892
46. Arndt, M.; Dindarogìlu, M.; Schmalz, H.-G.; Hilt, G. Org. Lett. 2011, 13, 6236
47. Coulter, M. M.; Dornan, P. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 6932
48. González-Rodríguez, C.; Pawley, R. J.; Chaplin, A. B.; Thompson, A. L.; Weller, A. S.; Willis, M. C. Angew. Chem., Int. Ed. 2011, 50, 5134
49. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
50. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209
51. Zhou, N.; Polozov, A. M.; O'Connell, M.; Burgeson, J.; Yu, P.; Zeller, W.; Zhang, J.; Onua, E.; Ramirez, J.; Palsdottir, G. A.; Halldorsdottir, G. V.; Andresson, T.; Kiselyov, A. S.; Gurney, M.; Singh, J. Bioorg. Med. Chem. Lett. 2010, 20, 2658
52. Lozinskaya, N. A.; Sosonyuk, S. E.; Volkova, M. S.; Seliverstov, M. Yu.; Proskurnina, M. V.; Bachurin, S. E.; Zefirov, N. S. Synthesis 2011, 273
53. Chen, X.-H.; Wei, Q.; Luo, S.-W.; Xiao, H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 13819
54. Grigg, R.; Whitney, S.; Sridharan, V.; Keep, A.; Derrick, A. Tetrahedron 2009, 65, 4375
55. Huang, A.; Kodanko, J. J.; Overman, L. E. J. Am. Chem. Soc. 2004, 126, 14043
56. Jossang, A.; Jossang, P.; Hadi, H. A.; Sévenet, T.; Bodo, B. J. Org. Chem. 1991, 56, 6527
57. Labroo, R. B.; Cohen, L. A. J. Org. Chem. 1990, 55, 4901
58. Jones, G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, UK, 1996; p 167.
59. Chen, M.-H.; Fitzgerald, P.; Singh, S. B.; O'Neill, E. A.; Schwartz, C. D.; Thompson, C. M.; O'Keefe, S. J.; Zaller, D. M.; Doherty, J. B. Bioorg. Med. Chem. Lett. 2008, 18, 2222
60. Harmata, M.; Hong, X. Org. Lett. 2007, 9, 2701
61. Turner, K. L.; Baker, T. M.; Islam, S.; Procter, D. J.; Stefaniak, M. Org. Lett. 2006, 8, 329
62. Uchida, R.; Imasoto, R.; Shiomi, K.; Tomoda, H.; Omura, S. Org. Lett. 2005, 7, 5701
63. Oshiro, Y.; Sakurai, Y.; Sato, S.; Kurahashi, N.; Tanaka, T.; Kikuchi, T.; Tottori, K.; Uwahodo, Y.; Miwa, T.; Nishi, T. J. Med. Chem. 2000, 43, 177
64. Semba, J.; Watanabe, A.; Kito, S.; Toru, M. Neuropharmacology 1995, 34, 785
65. Morita, S.; Irie, Y.; Saitoh, Y.; Kohri, H. Biochem. Pharmacol. 1976, 25, 1836
66. Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 26
67. Lavigne, G. Eur. J. Inorg. Chem. 1999, 917
68. Dombek, B. D. J. Organomet. Chem. 1989, 372, 151
69. Dombek, B. D. J. Organomet. Chem. 1983, 250, 467
70. Knifton, J. F. J. Am. Chem. Soc. 1981, 103, 3959
71. Dombek, B. D. J. Am. Chem. Soc. 1981, 103, 6508
72. Rivomanana, S.; Lavigne, G.; Lugan, N.; Bonnet, J.-J. Organometalllics 1991, 10, 2285
73. Han, S.-H.; Geoffroy, G. L.; Dombek, B. D.; Rheingold, A. L. Inorg. Chem. 1988, 27, 4355
74. Koelliker, R.; Bor, G. J. Organomet. Chem. 1991, 417, 439
75. Bor, G. Pure Appl. Chem. 1986, 58, 543