Cationic palladium(II)-catalyzed addition of arylboronic acids to nitriles. One-step synthesis of benzofurans from phenoxyacetonitriles

Organic Letters

Volumn 8, Issue 26, 2006, Pages 5987-5990

  Zhao, Baowei ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33846157728     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062438v     Document Type: Article

References (44)

1. For reviews, see: (a) Tsuji, J. Transition Metal Reagents and Catalysts; Wiley: Chichester, 2004.
2. (b) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 1998.
3. (c) de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; John Wiley & Sons: Weinheim, Germany, 2004.
4. (a) Tamaru, Y. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley: New York, 2002; Vol. 2, pp 1917-1943 and references therein.
5. (b) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 211.
6. (c) Hassen, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
7. (d) Culkin, D. A.; Hartiwig, J. F. Acc. Chem. Res. 2003, 36, 234.
8. (e) Tsuji, J. Palladium in Organic Synthesis; Springer: New York, 2005; p 211 and references therein.
9. (f) Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2005, 7, 2229.
10. (g) Kamijo, S.; Sasaki, Y.; Kanazawa, C.; Schüsseler, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2005, 44, 7718.
11. (a) Larock, R. C.; Tian, Q.; Pletnev, A. A. J. Am. Chem. Soc. 1999, 121, 3238.
12. (b) Pletnev, A. A.; Larock, R. C. Tetrahedron Lett. 2002, 43, 2133.
13. (c) Pletnev, A. A.; Tian, Q.; Larock, R. C. J. Org. Chem. 2002, 67, 9276.
14. (d) Pletnev, A. A.; Tian, Q.; Larock, R. C. J. Org. Chem. 2002, 67, 9428.
15. (e) Tian, Q.; Pletnev, A. A.; Larock, R. C. J. Org. Chem. 2003, 68, 339.
16. (f) Zhou, C.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 2302.
17. (g) Zhou, C.; Larock, R. C. J. Org. Chem. 2006, 71, 3551.
18. (h) Yang, C.-C.; Sun, P.-J.; Fang, J.-M. J. Chem. Soc., Chem. Commun. 1994, 2629.
19. (i) Yang, C.-C.; Tai, H.-M.; Sun, P.-J. Synlett 1997, 812.
20. (J) Yang, C.-C.; Tai, H.-M.; Sun, P.-J. J. Chem. Soc. Perkin Trans. 1 1997, 2843.
21. (k) Vicente, J.; Abad, J. A.; López-Sáez, M.-J.; Jones, P. G. Angew. Chem., Int. Ed. 2005, 44, 6001.
22. Zhao, L.; Lu, X. Angew. Chem., Int. Ed. 2002, 41, 4343.
23. Zhao, B.; Lu, X. Tetrahedron Lett. 2006, 47, 6765.
24. For reactions catalyzed by cationic palladium species, see: (a) Yamamoto, A. J. Organomet. Chem. 1995, 500, 337.
25. (b) Coates, G. W. Chem. Rev. 2000, 100, 1223.
26. (c) Widenhoefer, R. A. Acc. Chem. Res. 2002, 35, 905.
27. (d) Sodeoka, M.; Hamashima, Y. Bull. Chem. Soc. Jpn. 2005, 78, 941.
28. (e) Mikami, K.; Hatano, M.; Akiyama, K. Top. Organomet. Chem. 2005, 14, 279 and references therein.
29. For the reaction of arylboronic acids with a cationic palladium catalyst, see: (a) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
30. (b) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Organometallics 2004, 23, 4317.
31. Stang, P. J.; Cao, D. H.; Poulter, G. T.; Arif, A. M. Organometallics 1995, 14, 1110.
32. 10c
33. 2 has been reported in the literature, but no X-ray crystallographic data were given. See: (a) Vicente, J.; Abad, J.-A.; Gil-Rubio, J. Organometallics 1996, 15, 3509.
34. (b) Aeby, A.; Consiglio, G. Inorg. Chim. Acta 1999, 296, 45.
35. (c) Wimmer, S.; Castan, P.; Wimmer, F. L.; Johnson, N. P. Inorg. Chim. Acta 1988, 142, 13.
36. Guy, M.; Alois, V.; Richard, B. Tetrahedron Lett. 1994, 35, 3277.
37. (a) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240.
38. (b) Kina, A.; Iwamura, H.; Hayashi, T. J. Am. Chem. Soc. 2006, 128, 3904.
39. See, for example: Buu-Hoï, N. P. Ph.; Bisagni, E.; Royer, R.; Routier, C. J. Chem. Soc. 1957, 625.
40. (a) Black, D. S. C.; Craig, D. C.; Kumar, N.; Rezaie, R. Tehrahedron 1999, 55, 4803.
41. (b) Dehmlow, H.; Aebi, J. D.; Jolidon, S.; Ji, Y.-H.; von der Mark, E. M.; Himber, J.; Morand, O. H. J. Med. Chem. 2003, 46, 3354.
42. (c) Guthrie, R. W.; Kaplan, G. I.; Mennona, F. A.; Tilley, J. W.; Kierstead, R. W.; O'Donnell, M.; Crowley, H.; Yaremko, B.; Welton, A. F. J. Med. Chem. 1990, 33, 2856.
43. (d) Hambermann, J.; Ley, S. V.; Smits, R. J. Chem. Soc., Perkin Trans. 1 1999, 2421.
44. (e) Meshram, H. M.; Sekhar, K. C.; Ganesh, Y. S. S.; Yadav, J. S. Synlett 2000, 1273.