Regioselective synthesis of heteroaryl triflones by LDA (lithium diisopropylamide)-mediated anionic thia-Fries rearrangement

Organic Letters

Volumn 14, Issue 10, 2012, Pages 2544-2547

  Xu, Xiu Hua ^a   Wang, Xin ^a   Liu, Guo Kai ^a   Tokunaga, Etsuko ^a   Shibata, Norio ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84862098450     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300842d     Document Type: Article

References (69)

1. For the first example of an aryl ester-derived anionic Fries rearrangement, see: Miller, J. A. J. Org. Chem. 1987, 52, 322-323
2. For the first example of an aryl carbamate-derived anionic Fries rearrangement, see: Sibi, M. P.; Snieckus, V. J. Org. Chem. 1983, 48, 1935-1937
3. For the first example of an aryl phosphate ester-derived anionic Fries rearrangement, see: Melvin, L. S. Tetrahedron Lett. 1981, 22, 3375-3376
4. Hartung, C. G.; Snieckus, V. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, 2002; Chapter 10.
5. Snieckus, V. Chem. Rev. 1990, 90, 879-933
6. Taylor, C. M.; Watson, A. J. Curr. Org. Chem. 2004, 8, 623-636
7. Fries, K.; Finck, G. Ber. Dtsch. Chem. Ges. 1908, 41, 4271-4284
8. For a recent review, see: Sartori, G.; Maggi, R. Chem. Rev. 2011, 111, PR181-PR214
9. Anderson, J. C.; Reese, C. B. Proc. Chem. Soc. 1960, 217
10. For a recent review, see: Miranda, M. A.; Galindo, F. Mol. Supramol. Photochem. 2003, 9, 43-131
11. Macklin, T. K.; Panteleev, J.; Snieckus, V. Angew. Chem., Int. Ed. 2008, 47, 2097-2101
12. Ding, F.; Zhang, Y.-D.; Qu, B.; Li, G.-S.; Farina, V.; Lu, B. Z.; Senanayake, C. H. Org. Lett. 2008, 10, 1067-1070
13. Assimomytis, N.; Sariyannis, Y.; Stavropoulos, G.; Tsoungas, P. G.; Varvounis, G.; Cordopatis, P. Synlett 2009, 2777-2782
14. Miller, R. E.; Rantanen, T.; Ogilvie, K. A.; Groth, U.; Snieckus, V. Org. Lett. 2010, 12, 2198-2201
15. Wessels, M.; Mahajan, V.; Boßhammer, S.; Raabe, G.; Gais, H.-J. Eur. J. Org. Chem. 2011, 2431-2449
16. Jeong, Y.-C.; Moloney, M. G. J. Org. Chem. 2011, 76, 1342-1354
17. Chang, C.-W.; Chein, R.-J. J. Org. Chem. 2011, 76, 4154-4157
18. Henry, K. M.; Townsend, C. A. J. Am. Chem. Soc. 2005, 127, 3300-3309
19. Neufeind, S.; Hülsken, N.; Neudörfl, J.-M.; Schlörer, N.; Schmalz, H.-G. Chem.-Eur. J. 2011, 17, 2633-2641
20. Lin, Y.-C.; Lin, C.-H.; Chen, C.-Y.; Sun, S.-S.; Pal, B. Org. Biomol. Chem. 2011, 9, 4507-4517
21. Slana, G. B. C. A.; Azevedo, M. S.; Lopes, R. S. C.; Lopes, C. C.; Cardoso, J. N. Beilstein J. Org. Chem. 2006, 2, No. 1
22. Azzena, U.; Pisano, L.; Pittalis, M. Appl. Organomet. Chem. 2008, 22, 523-528
23. Berchel, M.; Salaün, J.-Y.; Couthon-Gourvès, H.; Haelters, J.-P.; Jaffrès, P.-A. Dalton Trans. 2010, 39, 11314-11316
24. Reed, M. A.; Chang, M. T.; Snieckus, V. Org. Lett. 2004, 6, 2297-2300
25. Macklin, T. K.; Reed, M. A.; Snieckus, V. Eur. J. Org. Chem. 2008, 1507-1509
26. James, C. A.; Snieckus, V. J. Org. Chem. 2009, 74, 4080-4093
27. Pitchumani, K.; Pandian, A. J. Chem. Soc., Chem. Commun. 1990, 1613-1614
28. Das, B.; Madhusudhan, P.; Venkataiah, B. J. Chem. Res., Synop. 2000, 200-201
29. Moghaddam, F. M.; Dakamin, M. G. Tetrahedron Lett. 2000, 41, 3479-3481
30. Benson, G.; Maughan, P. J.; Shelly, D. P.; Spillane, W. J. Tetrahedron Lett. 2001, 42, 8729-8731
31. Sharghi, H.; Shahsavari-Fard, Z. Helv. Chim. Acta 2005, 88, 42-52
32. Kato, J.; Maekawa, Y.; Yoshida, M. Chem. Lett. 2005, 34, 266-267
33. Kato, J.; Kakehata, H.; Maekawa, Y.; Yamashita, T. Chem. Commun. 2006, 4498-4500
34. Crevatín, L. K.; Bonesi, S. M.; Erra-Balsells, R. Helv. Chim. Acta 2006, 89, 1147-1157
35. Charmant, J. P.; Dyke, A. M.; Lloyd-Jones, G. C. Chem. Commun. 2003, 380-381
36. Zhao, Z.; Messinger, J.; Schön, U.; Wartchow, R.; Butenschön, H. Chem. Commun. 2006, 3007-3009
37. Kargbo, R.; Takahashi, Y.; Bhor, S.; Cook, G. R.; Lloyd-Jones, G. C.; Shepperson, I. R. J. Am. Chem. Soc. 2007, 129, 3846-3847
38. Barta, K.; Franciò, G.; Leitner, W.; Lloyd-Jones, G. C.; Shepperson, I. R. Adv. Synth. Catal. 2008, 350, 2013-2023
39. Dyke, A. M.; Gill, D. M.; Harvey, J. N.; Hester, A. J.; Lloyd-Jones, G. C.; Muñoz, M. P.; Shepperson, I. R. Angew. Chem., Int. Ed. 2008, 47, 5067-5070
40. Kruck, M.; Munoz, M. P.; Bishop, H. L.; Frost, C. G.; Chapman, C. J.; Kociok-Köhn, G.; Butts, C. P.; Lloyd-Jones, G. C. Chem.-Eur. J. 2008, 14, 7808-7812
41. Werner, G.; Lehmann, C. W.; Butenschön, H. Adv. Synth. Catal. 2010, 352, 1345-1355
42. Yoshioka, E.; Kohtani, S.; Miyabe, H. Org. Lett. 2010, 12, 1956-1959
43. Park, C.-M.; Bruncko, M.; Adickes, J.; Bauch, J.; Ding, H.; Kunzer, A.; Marsh, K. C.; Nimmer, P.; Shoemaker, A. R.; Song, X.; Tahir, S. K.; Tse, C.; Wang, X.; Wendt, M. D.; Yang, X.; Zhang, H.; Fesik, S. W.; Rosenberg, S. H.; Elmore, S. W. J. Med. Chem. 2008, 51, 6902-6915
44. Brown, B. S.; Keddy, R.; Zheng, G. Z.; Schmidt, R. G.; Koenig, J. R.; McDonald, H. A.; Bianchi, B. R.; Honore, P.; Jarvis, M. F.; Surowy, C. S.; Polakowski, J. S.; Marsh, K. C.; Faltynek, C. R.; Lee, C.-H. Bioorg. Med. Chem. 2008, 16, 8516-8525
45. Porrès, L.; Mongin, O.; Katan, C.; Charlot, M.; Pons, T.; Mertz, J.; Blanchard-Desce, M. Org. Lett. 2004, 6, 47-50
46. Droumaguet, C. L.; Mongin, O.; Werts, M. H. V.; Blanchard-Desce, M. Chem. Commun. 2005, 2802-2804
47. Mongin, O.; Porrès, L.; Charlot, M.; Katan, C.; Blanchard-Desce, M. Chem.-Eur. J. 2007, 13, 1481-1498
48. Sheppa, W. J. Am. Chem. Soc. 1963, 85, 1314-1318
49. Hendrickson, J. B.; Giga, A.; Wareing, J. J. Am. Chem. Soc. 1974, 96, 2275-2276
50. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195
51. Goumount, R.; Kizilian, E.; Buncel, E.; Terrier, F. Org. Biomol. Chem. 2003, 1, 1741-1748
52. Terrier, F.; Magnier, E.; Kizilian, E.; Wakselman, C.; Buncel, E. J. Am. Chem. Soc. 2005, 127, 5563-5571
53. Guesmi, N. E.; Boubaker, T.; Goumont, R.; Terrier, F. Org. Biomol. Chem. 2008, 6, 4041-4052
54. Xu, X.-H.; Liu, G.-K.; Azuma, A.; Tokunaga, E.; Shibata, N. Org. Lett. 2011, 13, 4854-4857
55. Kawai, H.; Sugita, Y.; Tokunaga, E.; Shibata, N. Eur. J. Org. Chem. 2012, 1295-1298
56. Matoba, K.; Kawai, H.; Furukawa, T.; Kusuda, A.; Tokunaga, E.; Nakamura, S.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2010, 49, 5762-5766
57. Ogawa, S.; Iida, N.; Tokunaga, E.; Shiro, M.; Shibata, N. Chem.-Eur. J. 2010, 16, 7090-7095
58. Huang, Y.; Tokunaga, E.; Suzuki, S.; Shiro, M.; Shibata, N. Org. Lett. 2010, 12, 1136-1138
59. Ogawa, S.; Nishimine, T.; Tokunaga, E.; Shibata, N. Synthesis 2010, 3274-3281
60. Kawai, H.; Tachi, K.; Tokunaga, E.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2011, 50, 7803-7806
61. Singh, K. J.; Collum, D. B. J. Am. Chem. Soc. 2006, 128, 13753-12760
62. Ma, Y.; Collum, D. B. J. Am. Chem. Soc. 2007, 129, 14818-14825
63. Riggs, J. C.; Singh, K. J.; Ma, Y.; Collum, D. B. J. Am. Chem. Soc. 2008, 130, 13709-13717
64. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748-8758
65. Peddibhotla, S. Curr. Bioact. Compd. 2009, 5, 20-28
66. Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381-1407
67. Kimata, A.; Nakagawa, H.; Ohyama, R.; Fukuuchi, T.; Ohta, S.; Suzuki, T.; Miyata, N. J. Med. Chem. 2007, 50, 5053-5056
68. Uramaru, N.; Shigematsu, H.; Toda, A.; Eyanagi, R.; Kitamura, S.; Ohta, S. J. Med. Chem. 2010, 53, 8727-8733
69. Chen, T.; Benmohamed, R.; Kim, J.; Smith, K.; Amante, D.; Morimoto, R. I.; Kirsch, D. R.; Ferrante, R. J.; Silverman, R. B. J. Med. Chem. 2012, 55, 515-527