FeCl3-mediated friedel-crafts hydroarylation with electrophilic N-acetyl indoles for the synthesis of benzofuroindolines

Angewandte Chemie - International Edition

Volumn 51, Issue 50, 2012, Pages 12546-12550

  Beaud, Rodolphe ^a   Guillot, Régis ^a   Kouklovsky, Cyrille ^a   Vincent, Guillaume ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

benzofuroindoline; diazonamide A; Friedel Crafts; indoles; umpolung

Indexed keywords

BENZOFUROINDOLINE; DIAZONAMIDE A; FRIEDEL-CRAFTS; INDOLES; UMPOLUNG;

FRIEDEL-CRAFTS REACTION;

ORGANIC COMPOUNDS;

ANTINEOPLASTIC AGENT; CHLORIDE; DIAZONAMIDE A; FERRIC CHLORIDE; FERRIC ION; FUSED HETEROCYCLIC RINGS; INDOLE; INDOLE DERIVATIVE; INDOLINE; OXAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CATALYSIS; CHLORIDES; FERRIC COMPOUNDS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDOLES; OXAZOLES; STEREOISOMERISM;

EID: 84870616076     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201206611     Document Type: Article

References (58)

1. N. Lindquist, W. Fenical, G. D. Van Duyne, J. Cjardy, J. Am. Chem. Soc. 1991, 113, 2303-2304
2. J. Li, A. W. Burgett, L. Esser, C. Amezscusa, P. G. Harran, Angew. Chem. 2001, 113, 4906-4909
3. Angew. Chem. Int. Ed. 2001, 40, 4770-4773
4. T.-S. Kam, S.-J. Tan, S.-W. Ng, K. Komiyama, Org. Lett. 2008, 10, 3749-3752
5. Q.-X. Wu, M. S. Crews, M. Draskovic, J. Sohn, T. A. Johnson, K. Tenney, F. A. Valeriote, X.-J. Yao, L. F. Bjeldanes, P. Crews, Org. Lett. 2010, 12, 4458-4461.
6. G. Wang, L. Shang, A. W. G. Burgett, P. G. Harran, X. Wang, Proc. Natl. Acad. Sci. USA 2007, 104, 2068-2073
7. N. S. Williams, A. W. G. Burgett, A. S. Atkins, X. Wang, P. G. Harran, S. L. McKnight, Proc. Natl. Acad. Sci. USA 2007, 104, 2074-2079.
8. M. Lachia, C. J. Moody, Nat. Prod. Rep. 2008, 25, 227-253; for representative examples, see
9. K. C. Nicolaou, M. Bella, D. Y.-K. Chen, X. Huang, T. Ling, S. A. Snyder, Angew. Chem. 2002, 114, 3645-3649
10. Angew. Chem. Int. Ed. 2002, 41, 3495-3499
11. Angew. Chem. 2002, 114, 3645-3649
12. K. C. Nicolaou, P. Bheema Rao, J. Hao, M. V. Reddy, G. Rassias, X. Huang, D. Y.-K. Chen, S. A. Snyder, Angew. Chem. 2003, 115, 1795-1800
13. Angew. Chem. Int. Ed. 2003, 42, 1753-1758
14. C.-M. Cheung, F. W. Goldberg, P. Magnus, C. J. Russell, R. Turnbull, V. Lynch, J. Am. Chem. Soc. 2007, 129, 12320-12327
15. C.-K. Mai, M. F. Sammons, T. Sammakia, Angew. Chem. 2010, 122, 2447-2450
16. Angew. Chem. Int. Ed. 2010, 49, 2397-2400
17. R. R. Knowles, J. Carpenter, S. B. Blakey, A. Kayano, I. K. Mangion, C. J. Sinz, D. W. C. MacMillan, Chem. Sci. 2011, 2, 308-311
18. W. Tian, L. Rao Chennamaneni, T. Suzuki, D. Y.-K. Chen, Eur. J. Org. Chem. 2011, 1027-1031.
19. A. W. G. Burgett, Q. Li, Q. Wei, P. G. Harran, Angew. Chem. 2003, 115, 5111-5116
20. Angew. Chem. Int. Ed. 2003, 42, 4961-4966.
21. For a low yielding intermolecular version, see:, K. C. Nicolaou, S. M. Dalby, S. Li, T. Suzuki, D. Y.-K. Chen, Angew. Chem. 2009, 121, 7752-7756
22. Angew. Chem. Int. Ed. 2009, 48, 7616-7620.
23. S. Zhu, D. W. C. Mac Millan, J. Am. Chem. Soc. 2012, 134, 10815-10818
24. K.-J. Wu, L.-X. Dai, S.-L. You, Org. Lett. 2012, 14, 3772-3775
25. J. Kim, M. Movassaghi, J. Am. Chem. Soc. 2011, 133, 14940-14943
26. L. Furst, J. M. R. Narayanam, C. R. J. Stephenson, Angew. Chem. 2011, 123, 9829-9833
27. Angew. Chem. Int. Ed. 2011, 50, 9655-9659
28. R. B. Bedford, N. Fey, M. F. Haddow, R. F. Sankey, Chem. Commun. 2011, 47, 3649-3651
29. V. R. Espejo, X.-B. Li, J. D. Rainier, J. Am. Chem. Soc. 2010, 132, 8282-8284
30. M. W. Boal, A. W. Schammel, N. K. Garg, Org. Lett. 2009, 11, 3458-3461
31. K. Eastman, P. S. Baran, Tetrahedron 2009, 65, 3149-3154
32. K. Matsumoto, H. Tokuyama, T. Fukuyama, Synlett 2007, 3137-3140
33. S. P. Govek, L. E. Overman, J. Am. Chem. Soc. 2001, 123, 9468-9469
34. F. Yamada, A. Goto, M. Somei, Heterocycles 2000, 53, 1255-1258.
35. Y. Kuninobu, T. Matsuki, K. Takai, J. Am. Chem. Soc. 2009, 131, 9914-9915
36. J. Kischel, I. Jovel, K. Mertins, A. Zapf, M. Beller, Org. Lett. 2006, 8, 19-22.
37. M. Bandini, A. Eischholzer, Angew. Chem. 2009, 121, 9786-9824
38. Angew. Chem. Int. Ed. 2009, 48, 9608-9644.
39. The addition of nucleophiles at the C2-position of indoles as the result of the preliminary activation of the C3-position by electrophiles is known; see:, C. C. J. Loh, D. Enders, Angew. Chem. 2012, 124, 46-49
40. Angew. Chem. Int. Ed. 2012, 51, 46-48.
41. Indoles substituted with electron-withdrawing groups at C3 can react with nucleophiles at C2; see:, L. Wang, Y. Shao, Y. Liu, Org. Lett. 2012, 14, 3978-3981.
42. K. Nishida, E. Yanase, S.-i. Nakatsuka, ITE Lett. Batteries New Technol. Med. 2006, 7, 59-62
43. N. Tajima, T. Hayashi, S.-N. Nakatsuka, Tetrahedron Lett. 2000, 41, 1059-1062.
44. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Rev. 2011, 111, 1293-1314
45. K. Komeyama, K. Aihara, T. Kashira, K. Takaki, Chem. Lett. 2011, 40, 1254-1256.
46. S. M. Bonesi, M. Fagnoni, Chem. Eur. J. 2010, 16, 13572-13589.
47. K. Ding, Y. Wang, L. Zhang, Y. Wu, T. Matsuura, Tetrahedron 1996, 52, 1005-1010.
48. CCDC 850422 (8 a), 850423 (3 g), and 850424 (16) contain the supplementary crystallographic data for 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.
49. 3, see:, S. Banerjee, B. C. Haldar, Nature 1950, 165, 1012.
50. T. Benkovics, I. A. Guzei, T. P. Yoon, Angew. Chem. 2010, 122, 9339-9343
51. Angew. Chem. Int. Ed. 2010, 49, 9153-9157.
52. A. Goti, M. Romani, Tetrahedron Lett. 1994, 35, 6567-6570.
53. G. Vincent, Y. Chen, J. W. Lane, R. M. Williams, Heterocycles 2007, 72, 385-398
54. X. Xu, X. Li, Org. Lett. 2009, 11, 1027-1029.
55. B. M. Trost, J. Quancard, J. Am. Chem. Soc. 2006, 128, 6314-6315
56. S. L. Crawley, R. L. Funk, Org. Lett. 2003, 5, 3169-3172.
57. W. E. Noland, F. J. Baude, J. Org. Chem. 1966, 31, 3321-3337
58. J. Bergman, N. Eklund, Tetrahedron 1980, 36, 1445-1450.