Palladium-Catalyzed C-H and C-N Arylation of Aminothiazoles with Arylboronic Acids

Asian Journal of Organic Chemistry

Volumn 2, Issue 11, 2013, Pages 938-942

  Uehara, Takahiro N ^a   Yamaguchi, Junichiro ^a   Itami, Kenichiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Azoles; C H arylation; C N arylation; Heteroarenes; Palladium

Indexed keywords

EID: 84896285797     PISSN: 21935807     EISSN: 21935807     Source Type: Journal    
DOI: 10.1002/ajoc.201300172     Document Type: Article

References (53)

1. J. Lee, S. J. Kim, H. Choi, Y. H. Kim, I. T. Lim, H. Yang, C. S. Lee, H. R. Kang, S. K. Ahn, S. K. Moon, D. Kim, S. Lee, N. S. Choi, K. J. Lee, J. Med. Chem. 2010, 53, 6337.
2. J. Lee, X. Wu, M. P. DiMagliano, E. C. Peters, Y. Wang, J. Hong, M. Hebrok, S. Ding, C. Y. Cho, P. G. Schultz, ChemBioChem 2007, 8, 1916.
3. A. Badorc, M.-F. Bordes, P. DeCointet, P. Savi, A. Bernat, A. Lalé, M. Petitou, J.-P. Maffrand, J.-M. Herbert, J. Med. Chem. 1997, 40, 3393.
4. T. Sanda, T. Okamoto, Y. Uchida, H. Nakagawa, S. Iida, S. Kayukawa, T. Suzuki, T. Oshizawa, T. Suzuki, N. Miyata, R. Ueda, Leukemia 2007, 21, 2344.
5. J. M. Herbert, G. Valette, A. Bernat, P. Savi, J. P. Maffrand, G. LeFur, Drugs Future 1992, 17, 1011.
6. A. Hantzsch, Justue Liebigs Ann. Chem. 1889, 269;
7. H. Erlenmeyer, Helv. Chim. Acta 1945, 28, 924.
8. S. P. Stanforth, Tetrahedron 1998, 54, 263;
9. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516;
10. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. Int. Ed. 2005, 44, 4442.
11. J. Hämmerle, M. Spina, M. Schnürch, M. D. Mihovilovic, P. Stanetty, Synthesis 2008, 3099.
12. S. Pivsa-Art, T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Bull. Chem. Soc. Jpn. 1998, 71, 467;
13. A. Mori, A. Sekiguchi, K. Masui, T. Shimada, M. Horie, K. Osakada, M. Kawamoto, T. Ikeda, J. Am. Chem. Soc. 2003, 125, 1700;
14. G. L. Turner, J. A. Morris, M. F. Greaney, Angew. Chem. 2007, 119, 8142;
15. G. L. Turner, J. A. Morris, M. F. Greaney, Angew. Chem. Int. Ed. 2007, 46, 7996;
16. L.-C. Campeau, M. Bertrand-Laperle, J.-P. Leclerc, E. Villemure, S. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 3276;
17. B. Liégault, D. Lapointe, L. Caron, A. Vlassova, K. Fagnou, J. Org. Chem. 2009, 74, 1826;
18. H. Hachiya, K. Hirano, T. Satoh, M. Miura, Angew. Chem. 2010, 122, 2248;
19. H. Hachiya, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2010, 49, 2202;
20. F. Shibahara, T. Yamauchi, E. Yamaguchi, T. Murai, J. Org. Chem. 2011, 76, 2680;
21. F. Shibahara, T. Yamauchi, E. Yamaguchi, T. Murai, J. Org. Chem. 2012, 77, 8815;
22. W. Han, P. Mayer, A. R. Ofial, Chem. Eur. J. 2011, 17, 6904;
23. W. Han, P. Mayer, A. R. Ofial, Angew. Chem. 2011, 123, 2226;
24. W. Han, P. Mayer, A. R. Ofial, Angew. Chem. Int. Ed. 2011, 50, 2178.
25. J. Canivet, J. Yamaguchi, I. Ban, K. Itami, Org. Lett. 2009, 11, 1733;
26. T. Yamamoto, K. Muto, M. Komiyama, J. Canivet, J. Yamaguchi, K. Itami, Chem. Eur. J. 2011, 17, 10113;
27. S. Yanagisawa, K. Itami, Tetrahedron 2011, 67, 4425;
28. K. Muto, J. Yamaguchi, K. Itami, J. Am. Chem. Soc. 2012, 134, 169;
29. K. Amaike, K. Muto, J. Yamaguchi, K. Itami, J. Am. Chem. Soc. 2012, 134, 13573.
30. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174;
31. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013;
32. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976;
33. L. Ackermann, R. Vicente, A. R. Kapdi, Angew.Chem. Int. Ed. 2009, 48, 9792;
34. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196;
35. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. Int. Ed. 2009, 48, 5094;
36. P. Thansandote, M. Lautens, Chem. Eur. J. 2009, 15, 5874;
37. T. Satoh, M. Miura, Synthesis 2010, 3395;
38. J. Bouffard, K. Itami, Top. Curr. Chem. 2010, 292, 231;
39. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. 2012, 124, 9092;
40. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. Int. Ed. 2012, 51, 8960;
41. J. Wencel-Delord, F. Glorius, Nat. Chem. 2013, 5, 369.
42. S. Kirchberg, S. Tani, K. Ueda, J. Yamaguchi, A. Studer, K. Itami, Angew. Chem. 2011, 123, 2435;
43. S. Kirchberg, S. Tani, K. Ueda, J. Yamaguchi, A. Studer, K. Itami, Angew. Chem. Int. Ed. 2011, 50, 2387;
44. S. Tani, T.N. Uehara, J. Yamaguchi, K. Itami, Chem. Sci., DOI:10.1039/C3SC52199K
45. M. Steinmetz, K. Ueda, S. Grimme, J. Yamaguchi, S. Kirchberg, K. Itami, A. Studer, Chem. Asian J. 2012, 7, 1256.
46. The structure of 2, 5-diarylthiazole 4 was determined by X-ray crystal structure analysis. A CIF file for 4 was deposited with the Cambridge Crystallographic Data Centre. CCDC957760 contains 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.
47. S. B. Blakey, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 6046;
48. J. Liu, M. J. Robins, Org. Lett. 2004, 6, 3421;
49. T. Saeki, E.-C. Son, K. Tamao, Org. Lett. 2004, 6, 617;
50. S. Ueno, N. Chatani, F. Kakiuchi, J. Am. Chem. Soc. 2007, 129, 6098;
51. T. Koreeda, T. Kochi, F. Kakiuchi, J. Am. Chem. Soc. 2009, 131, 7238;
52. M.-K. Zhu, J.-F. Zhao, T.-P. Loh, Org. Lett. 2011, 13, 6308;
53. T. Koreeda, T. Kochi, F. Kakiuchi, Organometallics 2013, 32, 682.