Palladium-catalyzed intramolecular coupling of arenes and unactivated alkanes in air

Organometallics

Volumn 27, Issue 19, 2008, Pages 4841-4843

  Liégault, Benoît ^a   Fagnou, Keith ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBONS; PALLADIUM;

ALKANE MOIETIES; AZOLE RING; COUPLING REACTIONS; INTRAMOLECULAR COUPLINGS; METHYL SUBSTITUENTS; PALLADIUM CATALYSTS; TERMINAL OXIDANTS; UNACTIVATED ALKANES;

PARAFFINS;

EID: 54249104878     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800780f     Document Type: Article

References (51)

1. For reviews, see: (a) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 2004.
2. (b) Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4544.
3. (c) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire. M. Chem. Rev. 2002, 102, 1359.
4. For reviews, see: (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
5. (b) Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200.
6. (c) Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrichim. Acta 2007, 40, 35.
7. (d) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
8. (e) Satoh, M.; Miura, M. Chem. Lett. 2007, 36, 200.
9. (f) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
10. (g) Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417.
11. (h) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013.
12. 2 couplings, see: (a) Lane, B. S.; Brown, M. A.; Sarnes, D. J. Am. Chem. Soc. 2005, 127, 8050.
13. (b) Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754.
14. (c) Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496.
15. (d) García-Cuadrado, D.; de Mendoza, P.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2007, 129, 6880.
16. 2 couplings, see: Yang, S.; Li, B.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 6066.
17. 3 couplings, see: (a) Ren, H.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 3462.
18. (b) Hitce, J.; Baudoin, Adv. Synth. Catal. 2007, 349, 2054.
19. (c) Lafrance, M.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570.
20. (d) Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2008, 10, 1759.
21. 3 couplings, see: (a) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
22. (b) Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007, 129, 3510.
23. (c) Wang, D.-H.; Wasa, M.; Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 7190.
24. For other metal-catalyzed couplings, see: (a) DeBoef, B.; Pastine, S. J.; Sames, D. J. Am. Chem. Soc. 2004, 126, 6556.
25. (b) Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K. J. Am. Chem. Soc. 2006, 128, 11748.
26. (c) Ackermann, L.; Born, R.; Álvarez-Bercedo, P. Angew. Chem., Int. Ed. 2007, 46, 6364.
27. (d) Özdemir, I.; Demir, S.; Çetinkaya, B.; Gourlaouen, C.; Maseras, F.; Bruneau, C.; Dixneuf, P. H. J. Am. Chem. Soc. 2008, 130, 1156.
28. (e) Lewis, J. C.; Berman, A. M.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 2493.
29. (f) Norinder, J.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 5858.
30. For a review on Pd(II)-catalyzed oxidative reactions, see: Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318.
31. For oxidative Heck reactions, see: (a) Jia, C.; Lu, W.; Kitamura, T.; Fujiwara, Y. Org. Lett. 1999, 1, 2097.
32. (b) Boele, M. D. K.; van Strijdonck, O. P. F.; De Vries, A. H. M.; Kamer, P. C. J.; De Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586.
33. (c) Zhang, H.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2004, 43, 6144.
34. (d) Yamada, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2005, 70, 5471.
35. (e) Capito, E.; Browna, J. M.; Ricci, A. Chem. Commun. 2005, 1854.
36. (f) Kong, A.; Han, X.; Lu, X. Org. Lett. 2006, 8, 1339.
37. (g) Beck, E. M.; Hatley, R.; Gaunt, M. J. Angew. Chem., Int. Ed. 2008, 47, 3004.
38. For recent examples, see: (a) Masui, K.; Ikegami, H.; Mon, A. J. Am. Chem. Soc. 2004, 126, 5074.
39. (b) Rong, Y.; Li, R.; Lu, W. Organometallics 2007, 26, 4376.
40. (c) Dwight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. Org. Lett. 2007, 9, 3137.
41. (d) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
42. (e) Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 11904.
43. (f) Stuart, D. R.; Villemure, E.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 12072.
44. (g) Xia, J.-B.; You, S.-L. Organometallics 2007, 26, 4869.
45. (h) Li, B.-J.; Tian. S.-L.; Fang, Z.; Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47, 1115.
46. (i) Liégault, B.; Lee, D.; Huestis, M. P.; Stuart, D. R.; Fagnou, K. J. Org. Chem. 2008, 73, 5022, and refs therein.
47. (a) Rong, Y.; Li, R.; Lu, W. Organometallics 2007, 26, 4376.
48. (b) Deng, G.; Zhao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2008, 47, 6278 See also ref 10e.
49. 101 the formation of six-membered rings by Pd-catalyzed intramolecular oxidative coupling has not yet been reported.
50. For a recent review on H/D exchange, see: Atzrodt, J.; Derdau, V.; Fey, T.; Zimmermann, J. Angew. Chem., Int. Ed. 2007, 46, 2.
51. Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1999, 121, 6616.