Room temperature copper(II)-catalyzed oxidative cyclization of enamides to 2,5-disubstituted oxazoles via vinylic C-H functionalization

Journal of Organic Chemistry

Volumn 77, Issue 17, 2012, Pages 7526-7537

  Cheung, Chi Wai ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C-H BOND; C-H FUNCTIONALIZATION; ENAMIDES; FUNCTIONALIZATIONS; HIGH YIELD; OXAZOLES; OXIDATIVE CYCLIZATION; REACTION PROTOCOLS; ROOM TEMPERATURE;

CATALYSIS; COPPER; IODINE;

CYCLIZATION;

1 (2 BROMOVINYL) 2 METHYLBENZENE; 1 (2 BROMOVINYL) 4 FLUOROBENZENE; 1 BROMO 4 (2 BROMOVINYL)BENZENE; 2 METHYL N (2 METHYLSTYRYL)BENZAMIDE; 3 (2 BROMOVINYL)THIOPHENE; 3 (3,4 DIMETHOXYPHENYL) N (4 METHOXYSTYRYL)ACRYLAMIDE; 3 NITRO N STYRYLBENZAMIDE; 4 (2 BENZAMIDOVINYL)PHENYL ACETATE; 4 (2 BROMOVINYL) 1,2 DIFLUOROBENZENE; 4 (2 BROMOVINYL)PHENYL ACETATE; 4 (TERT BUTYL) N (4 FLUOROSTYRYL)BENZAMIDE; 4 BROMO N (4 BROMOSTYRYL)BENZAMIDE; 4 CHLORO N STYRYLBENZAMIDE; 4 FLUORO N STYRYLBENZAMIDE; 4 METHOXY N STYRYLBENZAMIDE; 4 METHYL N STYRYLBENZAMIDE; 4 NITRO N STYRYLBENZAMIDE; 5 (2 BROMOVINYL) 1H INDOL 1 YL)(PHENYL)METHANONE; N (2 METHYLSTYRYL) 2 NAPHTHAMIDE; N (3,4 DIFLUOROSTYRYL) 3,4,5 TRIMETHOXYBENZAMIDE; N (4 CHLOROSTYRYL)BENZAMIDE; N (4 METHOXYSTYRYL)BENZAMIDE; N (4 METHYLSTYRYL)BENZAMIDE; N (4 PHENYLBUTA 1,3 DIEN 1 YL)BENZAMIDE; N (STYRYL)CINNAMAMIDE; N STYRYL 4 (TRIFLUOROMETHYL)BENZAMIDE; N STYRYLBENZAMIDE; N STYRYLPIVALAMIDE; OXAZOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; HYDROGEN BOND; ROOM TEMPERATURE; SUBSTITUTION REACTION;

AMIDES; CATALYSIS; COPPER; CYCLIZATION; MOLECULAR STRUCTURE; OXAZOLES; OXIDATION-REDUCTION; STEREOISOMERISM; TEMPERATURE;

EID: 84866061630     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301332s     Document Type: Article

References (85)

1. Jin, Z. Nat. Prod. Rep. 2011, 28, 1143
2. Zhang, J.; Ciufolini, M. A. Org. Lett. 2011, 13, 390
3. Wang, B.; Hansen, T. M.; Weyer, L.; Wu, D.; Wang, T.; Christmann, M.; Lu, Y.; Ying, L.; Engler, M. M.; Cink, R. D.; Lee, C.-S.; Ahmed, F.; Forsyth, C. J. J. Am. Chem. Soc. 2011, 133, 1506
4. Hashimoto, H.; Imamura, K.; Haruta, J.; Wakitani, K. J. Med. Chem. 2002, 45, 1511
5. Momose, Y.; Maekawa, T.; Yamano, T.; Kawada, M.; Odaka, H.; Ikeda, H.; Sohda, T. J. Med. Chem. 2002, 45, 1518
6. Brown, P.; Davies, D. T.; O'Hanlon, P. J.; Wilson, J. M. J. Med. Chem. 1996, 39, 446
7. Yang, W. S.; Shimada, K.; Delva, D.; Patel, M.; Ode, E.; Skouta, R.; Stockwell, B. R. ACS Med. Chem. Lett. 2012, 3, 35
8. Shaw, A. Y.; Henderson, M. C.; Flynn, G.; Samulitis, B.; Han, H.; Stratton, S. P.; Chow, H.-H. S.; Hurley, L. H.; Dorr, R. T. J. Pharmacol. Exp. Ther. 2009, 331, 636
9. Giddens, A. C.; Boshoff, H. I. M.; Franzblau, S. G.; Barry, C. E., III; Copp, B. R. Tetrahedron Lett. 2005, 46, 7355
10. Bey, E.; Marchais-Oberwinkler, S.; Kruchten, P.; Frotscher, M.; Werth, R.; Oster, A.; Algül, O.; Neugebauer, A.; Hartmann, R. W. Bioorg. Med. Chem. 2008, 16, 6423
11. For examples, see: Zhao, Q.; Liu, S.; Li, Y.; Wang, Q. J. Agric. Food Chem. 2009, 57, 2849
12. Min, J.; Lee, J. W.; Ahn, Y.-H.; Chang, Y.-T. J. Comb. Chem. 2007, 9, 1079
13. Grotkopp, O.; Ahmad, A.; Frank, W.; Müller, T. J. J. Org. Biomol. Chem. 2011, 9, 8130
14. Iliashenko, R. Y.; Gorobets, N. Y.; Doroshenko, A. O. Tetrahedron Lett. 2011, 52, 5086
15. Maier, G.; Schneider, J. M. Macromolecules 1998, 31, 1798
16. Gong, Z.-H.; Leu, C.-M.; Wu, F.-I.; Shu, C.-F. Macromolecules 2000, 33, 8527
17. Luo, Q.; Eibauer, S.; Reiser, O. J. Mol. Catal. A: Chem. 2007, 268, 65
18. Mazuela, J.; Paptchikhine, A.; Pàmies, O.; Andersson, P. G.; Diéguez, M. Chem. - Eur. J. 2010, 16, 4567
19. Mazuela, J.; Tolstoy, P.; Pàmies, O.; Andersson, P. G.; Diéguez, M. Org. Biomol. Chem. 2011, 9, 941
20. Turchi, I. J.; Dewar, M. J. S. Chem. Rev. 1975, 75, 389
21. Turchi, I. J. Ind. Eng. Chem. Prod. Res. Dev 1981, 20, 32
22. Revuelta, J.; Machetti, F.; Cicchi, S. In Modern Heterocyclic Chemistry; Alvarez-Builla, J.; Vaquero, J. J.; Barluenga, J., Eds.; Wiley-VCH Verlag & Co.: Weinheim, Germany, 2011; Vol. 2. For the recent examples of synthetic methods to oxazoles, see
23. Shi, B.; Blake, A. J.; Lewis, W.; Campbell, I. B.; Judkins, B. D.; Moody, C. J. J. Org. Chem. 2010, 75, 152
24. He, W.; Li, C.; Zhang, L. J. Am. Chem. Soc. 2011, 133, 8482
25. Cano, I.; álvarez, E.; Nicasio, M. C.; Pérez, P. J. J. Am. Chem. Soc. 2011, 133, 191
26. Xie, J.; Jiang, H.; Cheng, Y.; Zhu, C. Chem. Commun 2012, 48, 979
27. Xue, W.-J.; Li, Q.; Zhu, Y.-P.; Wang, J.-G.; Wu, A.-X. Chem. Commun. 2012, 48, 3485
28. Weyrauch, J. P.; Hashmi, A. S. K.; Schuster, A.; Hengst, T.; Schetter, S.; Littmann, A.; Rudolph, M.; Hamzic, M.; Visus, J.; Rominger, F.; Frey, W.; Bats, J. W. Chem. - Eur. J. 2010, 16, 956
29. Verrier, C.; Fiol-Petit, C.; Hoarau, C.; Marsais, F. Org. Biomol. Chem. 2011, 9, 6215
30. Li, Z.; Ma, L.; Xu, J.; Kong, L.; Wu, X.; Yao, H. Chem. Commun 2012, 48, 3763
31. Shin, C.; Sato, Y.; Sugiyama, H.; Nanjo, K.; Yoshimura, J. Bull. Chem. Soc. Jpn. 1977, 50, 1788
32. Das, J.; Reid, J. A.; Kronenthal, D. R.; Singh, J.; Pansegrau, P. D.; Mueller, R. H. Tetrahedron Lett. 1992, 33, 7835
33. Chattopadhyay, S. K.; Kempson, J.; McNeil, A.; Pattenden, G.; Reader, M.; Rippon, D. E.; Waite, D. J. Chem. Soc. Perkin Trans. 1 2000, 2415
34. Schuh, K.; Glorius, F. Synthesis 2007, 15, 2297
35. Ferreira, P. M. T.; Monteiro, L. S.; Pereira, G. Eur. J. Org. Chem. 2008, 4676
36. Ferreira, P. M. T.; Castanheira, E. M. S.; Monteiro, L. S.; Pereira, G.; Vilaça, H. Tetrahedron 2010, 66, 8672
37. Misra, N. C.; Ila, H. J. Org. Chem. 2010, 75, 5195
38. Martin, R.; Cuenca, A.; Buchwald, S. L. Org. Lett. 2007, 9, 5521
39. Zhou, H.; Chung, W.-J.; Xu, Y.-H.; Loh, T.-P. Chem. Commun. 2009, 3472
40. Yang, L.; Lei, C.-H.; Wang, D.-X.; Huang, Z.-T.; Wang, M.-X. Org. Lett. 2010, 12, 3918
41. Xu, Y.-H.; Chok, Y. K.; Loh, T.-P. Chem. Sci. 2011, 2, 1822
42. Besset, T.; Kuhl, N.; Patureau, F. W.; Glorius, F. Chem. - Eur. J. 2011, 17, 7167
43. Zhang, H.-J.; Bolm, C. Org. Lett. 2011, 13, 3900
44. Hesp, K. D.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2011, 133, 11430
45. Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062
46. Shi, Z.; Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3381
47. Ueda, S.; Nagasawa, H. Angew. Chem., Int. Ed. 2008, 47, 6411
48. Ueda, S.; Nagasawa, H. J. Org. Chem. 2009, 74, 4272
49. Guru, M. M.; Ali, M. A.; Punniyamurthy, T. J. Org. Chem. 2011, 76, 5295
50. Xiao, B.; Gong, T.-J.; Liu, Z.-J.; Liu, J.-H.; Luo, D.-F.; Xu, J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 9250
51. Wendlandt, A. E.; Stahl, S. S. Org. Biomol. Chem. 2012, 10, 3866
52. 2-catalyzed reactions. For example, see: Ye, F.; Shi, Y.; Zhou, L.; Xiao, Q.; Zhang, Y.; Wang, J. Org. Lett. 2011, 13, 5020
53. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
54. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
55. Kirk, K. L. Org. Process. Res. Dev. 2008, 12, 305
56. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475
57. Roy, S.; Gregg, B. T.; Gribble, G. W.; Le, V.-D.; Roy, S. Tetrahedron 2011, 67, 2161
58. Axelrod, B.; Belzile, J. R. J. Org. Chem. 1958, 23, 919
59. Karimoto, R. S.; Axelrod, B.; Wolinsky, J.; Schall, E. D. Phytochemistry 1964, 3, 349
60. Doyle, M. P.; Buhro, W. E.; Davidson, J. G.; Elliott, R. C.; Hoekstra, J. W.; Oppenhuizen, M. J. Org. Chem. 1980, 45, 3657
61. Besselièvre, F.; Piguel, S.; Mahuteau-Betzer, F.; Grierson, D. S. Org. Lett. 2008, 10, 4029
62. Fulmer, G. R.; Miller, A. J. M.; Sherden, N. H.; Gottlieb, H. E.; Nudelman, A.; Stoltz, B. M.; Bercaw, J. E.; Goldberg, K. I. Organometallics 2010, 29, 2176
63. Chowdhury, S.; Roy, S. Tetrahedron Lett. 1996, 37, 2623
64. Furuyama, T.; Yonehara, M.; Arimoto, S.; Kobayashi, M.; Matsumoto, Y.; Uchiyama, M. Chem. - Eur. J. 2008, 14, 10348
65. Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021
66. Linder, J.; Blake, A. J.; Moody, C. J. Org. Biomol. Chem. 2008, 6, 3908
67. Telvekar, V. N.; Chettiar, S. N. Tetrahedron Lett. 2007, 48, 4529
68. Pawluć?, P.; Hreczycho, G.; Szudkowska, J.; Kubicki, M.; Marciniec, B. Org. Lett. 2009, 11, 3390
69. Bull, J. A.; Mousseau, J. J.; Charette, A. B. Org. Lett. 2008, 10, 5485
70. Janssen Pharmaceutica, N. V.; Anzalone, L.; Feibush, P.; Dorziotis, I. K.; Li, X.; Villani, F. J. PCT Int. Appl., 2010051372, 06 May 2010.
71. Sinha, J.; Layek, S.; Mandal, G. C.; Bhattacharjee, M. Chem. Commun. 2001, 1916
72. Li, C.-W.; Lin, G.-Y.; Liu, R.-S. Chem. - Eur. J. 2010, 16, 5803
73. Rahman, S. M. A.; Sonoda, M.; Ono, M.; Miki, K.; Tobe, Y. Org. Lett. 2006, 8, 1197
74. Guillon, R.; Giraud, F.; Logé, C.; Borgne, M. L.; Picot, C.; Pagniez, F.; Pape, P. L. Bioorg. Med. Chem. Lett. 2009, 19, 5833
75. Bolshan, Y.; Batey, R. A. Angew. Chem., Int. Ed. 2008, 47, 2109
76. Katritzky, A. R.; Ignatchenko, A. V.; Lang, H. Synth. Commun. 1995, 25, 1197
77. Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955
78. Gooßen, L. J.; Salih, K. S. M.; Blanchot, M. Angew. Chem., Int. Ed. 2008, 47, 8492
79. Alonso, D. A.; Alonso, E.; Nájera, C.; Yus, M. Synlett 1997, 5, 491
80. Wan, C.; Gao, L.; Wang, Q.; Zhang, J.; Wang, Z. Org. Lett. 2010, 12, 3902
81. Jiang, H.; Huang, H.; Cao, H.; Qi, C. Org. Lett. 2010, 12, 5561
82. Beletskii, E. V.; Kuznetsov, M. A. Russ. J. Org. Chem. 2009, 45, 1229
83. Besselièvre, F.; Lebrequier, S.; Mahuteau-Betzer, F.; Piguel, S. Synthesis 2009, 20, 3511
84. Kuznetsov, M. A.; Voronin, V. V. Chem. Heterocycl. Compd. 2011, 47, 173
85. Flegeau, E. F.; Popkin, M. E.; Greaney, M. F. Org. Lett. 2008, 10, 2717