Synthesis of substituted biaryls via Suzuki, Stille and Hiyama cross-coupling and homo-coupling reactions by CN-dimeric and monomeric ortho-palladated catalysts

Applied Organometallic Chemistry

Volumn 27, Issue 7, 2013, Pages 412-418

  Hajipour, Abdol R ^a,b   Rafiee, Fatemeh ^a  

^a ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

^b UNIVERSITY OF WISCONSIN SCHOOL OF MEDICINE AND PUBLIC HEALTH   (United States)

Author keywords

biaryls; Hiyama reaction; palladated catalyst; Stille reaction; Suzuki reaction

Indexed keywords

BIARYLS; CROSS COUPLING REACTIONS; HIYAMA CROSS COUPLINGS; HIYAMA REACTION; HOMOCOUPLING REACTIONS; HOMOGENEOUS METAL CATALYSTS; STILLE REACTIONS; SUZUKI REACTION;

CATALYSTS; CHLORINE COMPOUNDS; METAL HALIDES; PALLADIUM COMPOUNDS;

CHEMICAL REACTIONS;

EID: 84879416709     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.2997     Document Type: Article

References (49)

1. S. Peter, H. Gerhard, P. Michael, W. Karl-Otto, Z. Cyrill, Chimia 2003, 57, 715.
2. G. Bringmann, S. Rudenauer, T. Bruhn, L. Benson, R. Brun, Tetrahedron 2008, 64, 5563.
3. J. G. Lei, G. Q. Lin, Chin. J. Chem. 2002, 20, 1263.
4. J. M. Lehn, Supramolecular Chemistry, 1st edn, VCH, Weinheim, 1995.
5. Y. Chao, G. R. Weisman, G. D. Y. Sogah, D. J. Cram, J. Am. Chem. Soc. 1979, 101, 4948.
6. J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359.
7. S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633.
8. P. Wawrzyniak, J. Heinicke, Tetrahedron Lett. 2006, 47, 8921.
9. I. Blaszczyk, A. M. Trzeciak, Tetrahedron 2010, 66, 9502.
10. a) A. F. Littke, L. Schwarz, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 6343
11. b) J. H. Li, Y. Liang, Y. X. Xie, Tetrahedron 2005, 61, 7289.
12. V. Polshettiwar, C. Len, A. Fihri, Coord. Chem. Rev. 2009, 253, 2599.
13. a) W. Su, S. Urgaonkar, P. A. McLaughlin, J. G. Verkade, J. Am. Chem. Soc. 2004, 126, 16433
14. b) W. Su, S. Urgaonkar, J. G. Verkade, Org. Lett. 2004, 6, 1421.
15. S. N. Chen, W. Y. Wu, F. Y. Tsai, Tetrahedron 2008, 64, 8164.
16. T. Hiyama, J. Organomet. Chem. 2002, 653, 58.
17. E. Alacid, C. Najera, Adv. Synth. Catal. 2006, 348, 2085.
18. T. D. Nelson, A. I. Meyers, J. Org. Chem. 1994, 59, 2655.
19. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
20. E. Negishi, Acc. Chem. Res. 1982, 15, 340.
21. V. Farina, Pure Appl. Chem. 1996, 68, 73.
22. V. Percec, J. Y. Bae, M. Zhao, D. H. Hill, J. Org. Chem. 1995, 60, 176.
23. N. Iranpoor, H. Firouzabadi, R. Azadi, J. Organomet. Chem. 2008, 693, 2469.
24. C. Qi, X. Sun, C. Lu, J. Yang, Y. Du, H. Wu, X. M. J. Zhang, J. Organomet. Chem. 2009, 694, 2912.
25. H. Tang, K. Menzel, G. C. Fu, Angew. Chem. Int. Ed. 2003, 42, 5079.
26. W. A. Herrmann, Angew. Chem. Int. Ed. 2002, 41, 1290.
27. R. B. Bedford, L. T. Pilarski, Tetrahedron Lett. 2008, 49, 4216.
28. K. K. Lo, C. Chung, T. K. Lee, L. Lui, K. H. Tang, N. Zhu, Inorg. Chem. 2003, 42, 6886.
29. A. Moyano, M. Rosol, R. M. Moreno, C. Lõpez, M. A. Maestro, Angew. Chem. Int. Ed. 2005, 44, 1865.
30. A. Zapf, M. Beller, Top. Catal. 2002, 19, 101.
31. C. O. Kappe, Angew. Chem. Int. Ed. 2004, 43, 6250.
32. B. K. Singh, N. Kaval, S. Tomar, E. V. Eycken, V. S. Parmar, Org. Process Res. Dev. 2008, 12, 468.
33. A. R. Hajipour, K. Karami, A. Pirisedigh, Inorg. Chim. Acta 2011, 370, 531.
34. A. R. Hajipour, K. Karami, F. Rafiee, Appl. Organomet. Chem. 2012, 26, 27.
35. E. Alacid, C. Nájera, Adv. Synth. Catal. 2006, 348, 945.
36. A. R. Hajipour, K. Karami, G. Tavakoli, Appl. Organomet. Chem. 2011, 25, 567.
37. A. R. Hajipour, F. Rafiee, Appl. Organomet. Chem. 2012, 26, 51.
38. A. R. Hajipour, F. Rafiee, A. E. Ruoho, Tetrahedron Lett. 2012, 53, 526.
39. A. R. Hajipour, F. Rafiee, J. Organomet. Chem. 2011, 696, 2669.
40. A. R. Hajipour, F. Rafiee, Synthetic Commun. 2013, 43, 1314.
41. K. Karami, C. Rizzoli, M. Mohamadi Salah, J. Organomet. Chem. 2011, 696, 940.
42. M. R. Eberhard, Org. Lett. 2004, 6, 2125.
43. D. E. Bergbreiter, P. L. Osburn, J. D. Frels, Adv. Synth. Catal. 2004, 347, 172.
44. L. Djakovitch, K. Köhler, J. G. de Vries, in Nanoparticles and Catalysis (Ed.:, D. Astruc,), Wiley-VCH, Weinheim, 2008, pp. 303.
45. M. T. Reetz, E. Westermann, Angew. Chem. Int. Ed. 2000, 39, 165.
46. T. Schareina, A. Zapf, M. Beller, J. Organomet. Chem. 2004, 689, 4576.
47. Y. Monguchi, Y. Fujita, S. Hashimoto, M. Ina, T. Takahashi, R. Ito, K. Nozaki, T. Maegawa, H. Sajiki, Tertrahedron 2011, 67, 8628.
48. N. Ma, Z. Duan, Y. Wu, J. Organomet. Chem. 2006, 691, 5697.
49. P. B. Silveira, V. R. Lando, J. Dupont, A. L. Monteiro, Tetrahedron Lett. 2002, 53, 2327.