Selectivity studies in the reaction between iodobenzene and phenylacetylene: Sonogashira coupling vs hydroarylation

Applied Organometallic Chemistry

Volumn 22, Issue 5, 2008, Pages 249-252

  Barros, José C ^a   De Souza, Andréa Luzia F ^a   De Lima, Paulo G ^a   Da Silva, Joaquim F M ^a   Antunes, O A C ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

C C coupling; Hydroarylation; Sonogashira reaction; Triarylethylenes

Indexed keywords

CATALYSTS; IONIC LIQUIDS; LIGANDS;

C-C COUPLING; HYDROARYLATION; PALLADIUM CATALYST; PHENYLBORONIC ACIDS; REACTION CONDITIONS; SONOGASHIRA COUPLING; SONOGASHIRA REACTIONS; TRIARYLETHYLENES;

AROMATIC HYDROCARBONS;

EID: 51349164019     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.1385     Document Type: Article

References (50)

1. K. Sonogashira, Cross-coupling reactions to sp carbon atoms, in Metal-Catalyzed Cross-Coupling Reactions (Eds: P. J. Stang, F. Diederich), Wiley-VCH: Weinheim, 1998, pp. 203-229;
2. b) B. Z. Lu, W. Zhao, H.-X. Wei, M. Dufour, V. Farina, C. H. Senanayake, Org. Lett. 2006; 8, 3271;
3. c) J. T. Guan, T. Q. Weng, G.-A. Yu, S. H. Liu, Tetrahedron Lett. 2007; 48, 7129;
4. d) K. Königsberger, G.-P. Chen, R. R. Wu, M. J. Girgis, K. Prasad, O. Repič, T. J. Blacklock, Org. Proc. Res. Dev. 2003; 7, 733;
5. e) S. Cacchi, G. Fabrizi, A. Gogglamani, J. Mol. Cat. A, Chemical 2004; 214, 57;
6. f) M. E. Cucciolito, A. D'Amora, A. Tuzi, A. Vitagliano, Organometallics 2007; 26, 5216;
7. g) E. Soriano, J. Marco-Contelles, Organometallics 2006; 25, 4542.
8. K. Sonogashira, Y. Tohda, N. Hagihara. Tetrahedron Lett. 1975; 16, 4467;
9. b) R. Chinchilla, C. Nájera, Chem. Rev. 2007; 107, 874;
10. c) H. Doucet, J.-C. Hierso, Angew. Chem. Int. Edn 2007; 46, 834;
11. d) S. Shi, Y. Zhang, Synlett 2007; 1843.
12. S. Cacchi, Pure Appl. Chem. 1990; 62, 713;
13. b) C. Nevado, A. M. Echavarren, Synthesis 2005; 167;
14. c) M. Ahlquist, G. Fabrizi, S. Cacchi, P.-O. Norrby, J. Am. Chem. Soc. 2006; 128, 12785.
15. F. I. M. Ginkel, J. Cornellsse, G. Lodder, J. Am. Chem. Soc. 1991; 113, 4261.
16. M. Dowsett, A. Howell, Nat. Med. 2002; 8, 1341.
17. H. Al-Inany, N. Johnson, Br. Med. J. 2006; 332, 1461.
18. R. Vardanyan, V. Hruby, Synthesis of Essential Drugs, Elsevier: Amsterdam, 2006, pp. 371-373.
19. R. M. Bryan, I. A. Mohammed, J. Org. Chem. 1985; 50, 2121.
20. P. L. Coe, C. E. Scriven, J. Chem. Soc., Perkin Trans. 1 1986; 475.
21. R. McCague, J. Chem. Soc., Perkin Trans. 1 1987; 1011.
22. R. Bucourt, C. Olier-Reuchet, D. J. Aitken, H.-P. Husson, Tetrahedron Lett. 1995; 36, 8221.
23. S. D. Brown, R. W. Armstrong, J. Org. Chem. 1997; 62, 7076.
24. R. A. Pilli, L. G. Robello, J. Braz. Chem. Soc. 2004; 115, 938.
25. E. Genin, V. Michelet, J.-P. Genet, J. Organomet. Chem. 2004; 689, 3820.
26. G. Takahashi, E. Shirakawa, T. Tsuchimoto, Y. Kawakami. Adv. Synth. Catal. 2006; 348, 837.
27. C. Zhou, D. E. Emrich, R. C. Larock, Org. Lett. 2003; 5, 1579;
28. b) C. H. Oh, H. H. Jung, K. S. Kim, N. Kim Angew. Chem. Int. Edn 2003, 42, 805;
29. d) C. M. Nunes, D. Steffens, A. L. Monteiro, Synlett 2007; 103.
30. S. Cacchi, M. Felici, B. Pietroni, Tetrahedron Lett. 1984; 25, 3137.
31. Y. Li, X. M. Hong, D. M. Collard, M. A. El-Sayed, Org. Lett. 2000; 2, 2385.
32. M. B. Thathagar, G. Rothenberg, Org. Biomol. Chem. 2006; 4, 111;
33. b) J. T. Guan, T. Q. Weng, G. A. Yu, S. Hua, Tetrahedron Lett. 2007; 48, 7129.
34. L. X. Yin, J. Liebscher, Chem. Rev. 2007; 107, 133.
35. B. L. Oliveira, O. A. C. Antunes, Lett. Org. Chem. 2007; 4, 13;
36. b) A. V. Coelho, A. L. F. Souza, P. G. Lima, J. L. Wardell, O. A. C. Antunes, Tetrahedron Lett. 2007; 48, 7671;
37. c) H. Brunner, N. Le Cousturier de Courcy, J.-P. Genêt, Tetrahedron Lett. 1999; 40, 4815.
38. R. Perez, D. Veronese, F. Coelho, O. A. C. Antunes, Tetrahedron Lett. 2006; 47, 1325.
39. S. Bräse, M. Schroen, Angew. Chem. Int. Edn 1999; 38, 1071.
40. S. Sengupta, S. K. Sadhukhan, Tetrahedron Lett. 1985; 39, 715.
41. S. Sengupta, S. Bhattacharya, J. Chem. Soc., Perkin Trans. 1 1993; 1943.
42. M. Eckhardt, G. C. Fu, J. Am. Chem. Soc. 2003; 125, 13642;
43. b) J. Zhong, J.-H. Xie, A.-E. Wang, W. Zhang, Q.-L. Zhou, Synlett 2006; 1193;
44. c) J. Guan, G.-A.Yu, J.-G. Hou, N. Yu, Y. Ren, S. H. Liu, Appl. Organomet. Chem. 2007, 21, 355;
45. d) O. Kühl, Chem. Soc. Rev. 2007; 36, 592;
46. e) J.-C. Hierso, J. Boudon, M. Picquet, P. Meunier, Eur. J. Org. Chem. 2007; 583.
47. M.-J. Wu, L.-M. Wei, C.-F. Lee, S.-P. Leou, L. L. Wei, Tetrahedron 2001; 57, 7839.
48. J.-C. Hierso, M. Picquet, H. Cattey, P. Meunier, Synlett 2006; 3005.
49. L. I. Smith, M. M. Falkof, Org. Synth. 1946; 22, 50.
50. D. J. Ager, J. Chem. Soc., Perkin Trans. 1 1986; 183.