Palladium-catalyzed direct 5-arylation of 1,3-dimethyluracil with aryl bromides: An electrophilic metalation-deprotonation with electrophilic arylpalladium intermediate

Tetrahedron Letters

Volumn 52, Issue 47, 2011, Pages 6228-6233

  Kim, Ko Hoon ^a   Lee, Hyun Seung ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

Direct arylation; Electrophilic metalation deprotonation; Palladium; Uracil

Indexed keywords

1,3 DIMETHYLURACIL; BROMINE DERIVATIVE; ELECTROPHILE; METAL; PALLADIUM;

ARTICLE; ARYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON TRANSPORT; QUANTUM YIELD; REACTION ANALYSIS;

EID: 80054870897     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.09.066     Document Type: Article

References (54)

1. For the biological activities of 5-aryluracil derivatives, see: C.F. Regan, Z. Guo, Y. Chen, C.Q. Huang, M. Chen, W. Jiang, J.K. Rueter, T. Coon, C. Chen, J. Saunders, M.S. Brown, S.F. Betz, R.S. Strutheres, C. Yang, J. Wen, A. Madan, and Y.-F. Zhu Bioorg. Med. Chem. Lett. 18 2008 4503 4507
2. C. Chen, D. Wu, Z. Guo, Q. Xic, G.J. Reinhart, A. Madan, J. Wen, T. Chen, C.Q. Huang, M. Chen, Y. Chen, F.C. Tucci, M. Rowbottom, J. Pontillo, Y.-F. Zhu, W. Wade, J. Saunders, H. Bozigian, and R.S. Struthers J. Med. Chem. 51 2008 7478 7485
3. Z. Guo, Y. Chen, C.Q. Huang, T.D. Gross, J. Pontillo, M.W. Rowbottom, J. Saunders, S. Struthers, F.C. Tucci, Q. Xie, W. Wade, Y.-F. Zhu, D. Wu, and C. Chen Bioorg. Med. Chem. Lett. 15 2005 2519 2522
4. C. Chen, Y. Chen, J. Pontillo, Z. Guo, C.Q. Huang, D. Wu, A. Madan, T. Chen, J. Wen, Q. Xie, F.C. Tucci, M. Rowbottom, Y.-F. Zhu, W. Wade, J. Saunders, H. Bozigian, and R.S. Struthers Bioorg. Med. Chem. Lett. 18 2008 3301 3305
5. Y. Yamamoto, T. Seko, and H. Nemoto J. Org. Chem. 54 1989 4734 4736
6. For the applications of 5-aryluracil derivatives in bioanalysis or chemical biology, see: H. Cahova, L. Havran, P. Brazdilova, H. Pivonkova, R. Pohl, M. Fojta, and M. Hocek Angew. Chem., Int. Ed. 47 2008 2059 2062
7. M. Fukuda, M. Nakamura, T. Takada, and K. Yamana Tetrahedron Lett. 51 2010 1732 1735
8. M.F. Jacobsen, E.E. Ferapontova, and K.V. Gothelf Org. Biomol. Chem. 7 2009 905 908
9. C. Wanninger-Weib, and H.-A. Wagenknecht Eur. J. Org. Chem. 2008 64 71
10. T. Ehrenschwender, and H.-A. Wagenknecht Synthesis 2008 3657 3662
11. N. Amann, E. Pandurski, T. Fiebig, and H.-A. Wagenknecht Chem. Eur. J. 8 2002 4877 4883
12. A. Okamoto, K. Tainaka, T. Unzai, and I. Saito Tetrahedron 63 2007 3465 3470
13. M.L. Capobianco, A. Cazzato, S. Alesi, and G. Barbarella Bioconjugate Chem. 19 2008 171 177
14. S.G. Srivatsan, and Y. Tor J. Am. Chem. Soc. 129 2007 2044 2053
15. N.J. Greco, and Y. Tor J. Am. Chem. Soc. 127 2005 10784 10785
16. For the palladium-catalyzed synthesis of 5-aryluracil derivatives with arylboron reagents, see: L. Kalachova, R. Pohl, and M. Hocek Synthesis 2009 105 112
17. E.C. Western, J.R. Daft, E.M. Johnson II, P.M. Gannett, and K.H. Shaughnessy J. Org. Chem. 68 2003 6767 6774
18. G.T. Crisp, and V. Macolino Synth. Commun. 20 1990 413 422
19. K. Pomeisl, A. Holy, R. Pohl, and K. Horska Tetrahedron 65 2009 8486 8492
20. K. Pomeisl, A. Holy, and R. Pohl Tetrahedron Lett. 48 2007 3065 3067
21. A. Coelho, and E. Sotelo J. Comb. Chem. 7 2005 526 529
22. For recent 6-arylation of uracil derivatives, see: Y.-C. Shih, and T.-C. Chien Tetrahedron 67 2011 3915 3923
23. For the palladium-catalyzed synthesis of 5-aryluracil derivatives with arylstannane reagents, see: A.J. Gutierrez, T.J. Terhorst, M.D. Matteucci, and B.C. Froehler J. Am. Chem. Soc. 116 1994 5540 5544
24. J.M. Sadler, O. Ojewoye, and K.L. Seley-Radtke Nucleic Acids Symp. Ser. 52 2008 571 572
25. P. Wigerinck, C. Pannecouque, R. Snoeck, E. De Clercq, and P. Herdewijn J. Med. Chem. 34 1991 2383 2389
26. P. Herdewijn, L. Kerremans, P. Wigerinck, F. Vandendriessche, and A.V. Aerschot Tetrahedron Lett. 32 1991 4397 4400
27. M. Cernova, R. Pohl, and M. Hocek Eur. J. Org. Chem. 2009 3698 3701
28. M. Cernova, I. Cerna, R. Pohl, and M. Hocek J. Org. Chem. 76 2011 5309 5319
29. Palladium-catalyzed intramolecular arylations of uracil derivatives have been reported in some cases, see: K.C. Majumdar, B. Sinha, P.K. Maji, and S.K. Chattopadhyay Tetrahedron 65 2009 2751 2756
30. K.C. Majumdar, P. Debnath, A. Taher, and A.K. Pal Can. J. Chem. 86 2008 325 332
31. For the palladium-catalyzed arylation of indole derivatives, see: N. Lebrasseur, and I. Larrosa J. Am. Chem. Soc. 130 2008 2926 2927
32. X. Wang, D.V. Gribkov, and D. Sames J. Org. Chem. 72 2007 1476 1479
33. B.S. Lane, and D. Sames Org. Lett. 6 2004 2897 2900
34. B.B. Toure, B.S. Lane, and D. Sames Org. Lett. 8 2006 1979 1982
35. E.T. Nadres, A. Lazareva, and O. Daugulis J. Org. Chem. 76 2011 471 483
36. For the 1,2-palladium migration, see: S. Kirchberg, R. Frohlich, and A. Studer Angew. Chem., Int. Ed. 48 2009 4235 4238
37. B.S. Lane, M.A. Brown, and D. Sames J. Am. Chem. Soc. 127 2005 8050 8057
38. For our recent example of palladium-catalyzed benzoin-mediated Ullmann type coupling of aryl bromides to biaryls B.R. Park, K.H. Kim, T.H. Kim, and J.N. Kim Tetrahedron Lett. 52 2011 4405 4407 and further references were cited therein. In the reaction, biaryls and trace amount of arenes were formed but the yields of these compounds were not determined
39. 3, see: S. Pivsa-Art, T. Satoh, Y. Kawamura, M. Miura, and M. Nomura Bull. Chem. Soc. Jpn. 71 1998 467 473
40. M. Watanabe, M. Nishiyama, T. Yamamoto, and Y. Koie Tetrahedron Lett. 41 2000 481 483
41. D.A. Safin, M.G. Babashkina, and A. Klein Catal. Lett. 129 2009 363 366
42. D.A. Safin, and M.G. Babashkina Catal. Lett. 130 2009 679 682
43. B. Glover, K.A. Harvey, B. Liu, M.J. Sharp, and M.F. Tymoschenko Org. Lett. 5 2003 301 304
44. 1-protected uracil derivatives with a tetrahydrofuranyl moiety, see: T. Maruyama, S. Kozai, Y. Demizu, M. Witvrouw, C. Pannecouque, J. Balzarini, R. Snoecks, G. Andrei, and E. De Clercq Chem. Pharm. Bull. 54 2006 325 333
45. N.P. Dolman, J.C.A. More, A. Alt, J.L. Knauss, O.T. Pentikainen, C.R. Glasser, D. Bleakman, M.L. Mayer, G.L. Collingridge, and D.E. Jane J. Med. Chem. 50 2007 1558 1570
46. N.P. Dolman, J.C.A. More, A. Alt, J.L. Knauss, H.M. Troop, D. Bleakman, G.L. Collingridge, and D.E. Jane J. Med. Chem. 49 2006 2579 2592
47. D. Engel, A. Nudelman, N. Tarasenko, I. Levovich, I. Makarovsky, S. Sochotnikov, I. Tarasenko, and A. Rephaeli J. Med. Chem. 51 2008 314 323
48. For the palladium-catalyzed oxidative arylation of indoles, see: D.R. Stuart, E. Villemure, and K. Fagnou J. Am. Chem. Soc. 129 2007 12072 12073
49. D.R. Stuart, and K. Fagnou Science 316 2007 1172 1175
50. S. Potavathri, K.C. Pereira, S.I. Gorelsky, A. Pike, A.P. LeBris, and B. DeBoef J. Am. Chem. Soc. 132 2010 14676 14681
51. T.A. Dwight, N.R. Rue, D. Charyk, R. Josselyn, and B. DeBoef Org. Lett. 9 2007 3137 3139
52. K. Seki, K. Matsuda, Y. Bando, and K. Ohkura Chem. Pharm. Bull. 36 1988 4737 4748
53. K. Ohkura, T. Sugaoi, K. Nishijima, Y. Kuge, and K. Seki Tetrahedron Lett. 43 2002 3113 3115
54. B.T. Keen, and W.W. Paudler J. Org. Chem. 40 1975 3717 3720