Palladium/2,2′-bipyridyl/Ag2CO3 catalyst for C-H bond arylation of heteroarenes with haloarenes

Tetrahedron

Volumn 67, Issue 24, 2011, Pages 4425-4430

  Yanagisawa, Shuichi ^a   Itami, Kenichiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

C H arylation; Catalysis; Heterobiaryl; Palladium

Indexed keywords

2,2' BIPYRIDINE; BENZOFURAN DERIVATIVE; CARBON; DIMETHYL SULFOXIDE; HYDROGEN; INDOLE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON; SILVER CARBONATE; SILVER DERIVATIVE; THIAZOLE; THIOPHENE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

EID: 79957517035     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.03.093     Document Type: Article

References (54)

1. I. McCulloch, M. Heeney, M.L. Chabinyc, D. DeLongchamp, J. Kline, M. Cölle, W. Duffy, D. Fischer, D. Gundlach, B. Hamadani, R. Hamilton, L. Richter, A. Salleo, M. Shukunov, D. Sparrowe, S. Tierney, and W. Zhang Adv. Mater. 21 2009 1091
2. P. Lloyd-Williams, and E. Giralt Chem. Soc. Rev. 30 2001 145
3. K.C. Nicolaou, P.G. Baulger, and D. Sarlah Angew. Chem., Int. Ed. 44 2005 4442
4. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, and M. Lemaire Chem. Rev. 102 2002 1359
5. A. de Meijere, and F. Diederich Metal-Catalyzed Cross-coupling Reactions 2nd ed. 2004 Wiley-VCH New York, NY
6. N. Miyaura Cross-Coupling Reactions: a Practical Guide 2002 Springer Berlin
7. Recent reviews on direct C-H bond arylation of (hetero)arenes:
8. D. Alberico, M.E. Scott, and M. Lautens Chem. Rev. 107 2007 174
9. L.-C. Campeau, D.R. Stuart, and K. Fagnou Aldrichimica Acta 40 2007 35
10. I.V. Seregin, and V. Gevorgyan Chem. Soc. Rev. 36 2007 1173
11. T. Satoh, and M. Miura Chem. Lett. 36 2007 200
12. L. Ackermann, R. Vicente, and A.R. Kapdti Angew. Chem., Int. Ed. 48 2009 9792
13. F. Bellina, and R. Rossi Tetrahedron 65 2009 10269
14. For selected recent breakthroughs, see:
15. D.R. Stuart, and K. Fagnou Science 316 2007 1172
16. R.J. Phipps, and M.J. Gaunt Science 323 2009 1593
17. J.C. Lewis, R.G. Bergman, and J.A. Ellman Acc. Chem. Res. 41 2008 1013
18. J. Norinder, A. Matsumoto, N. Yoshikai, and E. Nakamura J. Am. Chem. Soc. 130 2008 5858
19. H.-Q. Do, R.K.M. Khan, and O. Daugulis J. Am. Chem. Soc. 130 2008 15185
20. L. Ackermann, A. Althammer, and S. Fenner Angew. Chem., Int. Ed. 48 2009 201
21. L.-C. Campeau, D.R. Stuart, J.P. Leclerc, M. Bertrand-Laperle, E. Villemure, H.-Y. Sun, S. Lasserre, N. Guimond, M. Lecavallier, and K. Fagnou J. Am. Chem. Soc. 131 2009 3291
22. C. Wang, I. Piel, and F. Glorius J. Am. Chem. Soc. 131 2009 4194
23. K.L. Hull, and M.S. Sanford J. Am. Chem. Soc. 131 2009 9651
24. C. Huang, and V. Gevorgyan J. Am. Chem. Soc. 131 2009 10844
25. M. Tobisu, I. Hyodo, and N. Chatani J. Am. Chem. Soc. 131 2009 12070
26. M. Kim, J. Kwak, and S. Chang Angew. Chem., Int. Ed. 48 2009 8935
27. C.-L. Sun, B.-J. Li, and Z.-J. Shi Chem. Commun. 2010 677
28. B. Xiao, Y. Fu, J. Xu, T.-J. Gong, J.-J. Dai, J. Yi, and L. Liu J. Am. Chem. Soc. 132 2010 468
29. T. Nishikata, A.R. Abela, and B.H. Lipshutz Angew. Chem., Int. Ed. 49 2010 781
30. M. Wasa, B.T. Worrell, and J.-Q. Yu Angew. Chem., Int. Ed. 49 2010 1275
31. F. Vallée, J.J. Mousseau, and A.B. Charette J. Am. Chem. Soc. 132 2010 1514
32. W. Liu, H. Cao, and A. Lei Angew. Chem., Int. Ed. 49 2010 2004
33. P. Xi, F. Yang, S. Qin, D. Zhao, J. Lan, G. Gao, C. Hu, and J. You J. Am. Chem. Soc. 132 2010 1822
34. H. Hachiya, K. Hirano, T. Satoh, and M. Miura Angew. Chem., Int. Ed. 49 2010 2202
35. Our recent contributions. Review:
36. K. Itami J. Synth. Org. Chem. Jpn. 68 2010 1132
37. J. Bouffard, and K. Itami Top. Curr. Chem. 292 2010 231
38. Yanagisawa, S.; Itami, K. ChemCatChem, in press (doi:10.1002/cctc. 201000431 ). Rh:
39. S. Yanagisawa, T. Sudo, R. Noyori, and K. Itami J. Am. Chem. Soc. 128 2006 11748
40. S. Yanagisawa, T. Sudo, R. Noyori, and K. Itami Tetrahedron 64 2008 6073 Ir:
41. J. Benoît, T. Yamamoto, and K. Itami Angew. Chem., Int. Ed. 48 2009 3644 Cu:
42. I. Ban, T. Sudo, T. Taniguchi, and K. Itami Org. Lett. 10 2008 3607 Ni:
43. J. Canivet, J. Yamaguchi, I. Ban, and K. Itami Org. Lett. 11 2009 1733 Pd:
44. S. Yanagisawa, K. Ueda, H. Sekizawa, and K. Itami J. Am. Chem. Soc. 131 2009 14622
45. K. Ueda, S. Yanagisawa, J. Yamaguchi, and K. Itami Angew. Chem., Int. Ed. 49 2010 8946
46. S. Kirchberg, S. Tani, K. Ueda, J. Yamaguchi, A. Studer, and K. Itami Angew. Chem., Int. Ed. 50 2011 2387 KOtBu:
47. S. Yanagisawa, K. Ueda, T. Taniguchi, and K. Itami Org. Lett. 10 2008 4673
48. F. Shibahara, E. Yamaguchi, and T. Murai Chem. Commun. 2010 2471
49. 3, and KF in DMSO at 100 °C. For the purpose of elucidating the mechanism, they investigated several stoichiometric reactions of organopalladium complexes ligated by bipy.
50. A. Sugie, H. Furukawa, Y. Suzaki, K. Osakada, M. Akita, D. Monguchi, and A. Mori Bull. Chem. Soc. Jpn. 82 2009 555
51. A. Sugie, K. Kobayashi, Y. Suzaki, K. Osakada, and A. Mori Chem. Lett. 35 2006 1100
52. A. Mori, A. Sugie, H. Furukawa, Y. Suzaki, K. Osakada, and M. Akita Chem. Lett. 37 2008 542
53. 2(bipy)·DMSO (4)) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data-request/cif.
54. W.J.J. Smeets, A.L. Spek, J.L. Hoare, A.J. Canty, N. Hovestad, and G. van Koten Acta Crystallogr. C53 1997 1045