High-yielding palladium-catalyzed intramolecular alkane arylation: Reaction development and mechanistic studies

Journal of the American Chemical Society

Volumn 129, Issue 47, 2007, Pages 14570-14571

  Lafrance, Marc ^a   Gorelsky, Serge I ^a   Fagnou, Keith ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE;

ALKANES; CATALYSIS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PALLADIUM; PROTONS;

EID: 36749003741     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja076588s     Document Type: Article

References (54)

1. (a) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
2. (b) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
3. (c) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 211.
4. (d) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
5. (e) Campeau, L.-C.; Fagnou, K. Chem. Commun. 2005, 1253.
6. (f) Espino, C. G.; Du Bois, J. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005; pp 379-416.
7. (g) Davies, H. M. L. Angew. Chem., Int. Ed. 2006, 45, 6422.
8. (h) Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q.-N.; Lazareva, A. Synlett 2006, 3382.
9. (i) Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439.
10. (j) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
11. (k) Seregin, I. V.; Gevorgyan, V. J. Chem. Soc., Chem. Rev. 2007, 36, 1173.
12. (l) Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrich. Chim. Acta 2007, 40, 35.
13. (m) Godula, K.; Sames, D. Science 2006, 312, 67.
14. 3 C-H bonds, see: (a) 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.
15. (b) Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634.
16. (c) Hitce, J.; Retailleau, P.; Baudoin, O. Chem. Eur. J. 2007, 13, 792.
17. (d) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
18. (e) Shaabashov, D.; Daugulis, O. Org. Lett. 2005, 7, 3657.
19. (f) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
20. (g) DeBoef, B.; Pastine, S. J.; Sames, D. J. Am. Chem. Soc. 2004, 126, 6556.
21. (h) Baudoin, O.; Herrbach, A.; Gueritte, F. Angew. Chem., Int. Ed. 2003, 42, 5736.
22. (i) Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995.
23. For examples at benzylic C-H bonds, see: (j) Ren, H.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 3462.
24. (k) Dong, C.-G.; Hu, Q.-G. Angew. Chem., Int. Ed. 2006, 45, 2289.
25. (l) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
26. 3 C-H bonds next to heteroatoms, see: (m) Pastine, S. J.; Gribkov, D. V.; Sames, D. J. Am. Chem. Soc. 2006, 128, 14220.
27. (n) Dyker, G. J. Org. Chem. 1993, 58, 6426.
28. Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047.
29. (a) Lane, B. S.; Sames, D. Org. Lett. 2004, 6, 2897.
30. (b) Lanes, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050.
31. (c) Park, C.-H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
32. (a) Davies, D. L.; Donald, S. M. A.; Macgregor, S. A. J. Am. Chem. Soc. 2005, 127, 13754.
33. (b) Garcia-Cuadrado, D.; Braga, A. A. C.; Maeras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066.
34. (c) Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754.
35. Boller, T. M.; Murphy, J. M.; Hapke, M.; Ishiyama, T.; Miyaura, N.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 14263.
36. (a) Lersch, M.; Tislet, M. Chem. Rev. 2005, 105, 2471.
37. (b) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
38. For illustrative mechanistic work dealing with alkane oxidation, see: (a) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 5961.
39. (b) Siegbahn, P. E. M.; Crabtree, R. H. J. Am. Chem. Soc. 1996, 118, 4442.
40. (c) Zh, H.; Ziegler, T. J. Organomet. Chem. 2006, 691, 4486.
41. For example, see: (a) Kataoka, K.-I.; Shiota, T.; Takeyasu, T.; Minoshima, T.; Watanabe, K.; Tanaka, H.; Mochizuki, T.; Taneda, K.; Ota, M.; Tanabe, H.; Yamaguchi, H. J. Med. Chem. 1996, 39, 1262.
42. (b) Shi, G. Q.; Dropinski, J. F.; Zhang, Y.; Santini, C.; Sahoo, S. P.; Berger, J. P.; MacNaul, K. L.; Zhou, G.; Agrawal, A.; Alvaro, R.; Cai, T.-q.; Hernandez, M.; Wright, S. D.; Moller, D. E.; Heck, J. V.; Meinke, P. T. J. Med. Chem. 2005, 48, 5589.
43. (c) Tamura, K.; Kato, Y.; Ishikawa, A.; Kato, Y.; Himori, M.; Yoshida, M.; Takashima, Y.; Suzuki, T.; Kawabe, Y.; Cynshi, O.; Kodama, T.; Niki, E.; Shimizu, M. J. Med. Chem. 2003, 46, 3083.
44. (d) Ohkawa, S.; Fukatsu, K.; Miki, S.; Hashimoto, T.; Sakamoto, J.; Doi, T.; Nagai, Y.; Aono, T. J. Med. Chem. 1997, 40, 559.
45. For example, see: (a) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542.
46. (b) Giri, R.; Chen, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 2112.
47. Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496.
48. The most common route to simple analogues involves phenol alkylation with an appropriately substituted allyl fragment followed by a Claisen rearrangement and subsequent cationic ring closure. See for example ref 9a. This approach relies on sufficient substituent stabilization of the carbocation which cannot occur when electron-withdrawing groups are present.
49. See the Supporting Information for details.
50. Brookhart, M.; Green, M. L. H.; Parkin, G. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 6908.
51. (a) Sannigrahi, A. B.; Kar, T. Chem. Phys. Lett. 1990, 173, 569.
52. (b) Giambiagi, M.; Giambiagi, M. S.; Mundim, K. C. Struct. Chem. 1990, 1, 123.
53. Mayer, I. Chem. Phys. Lett. 1983, 97, 270.
54. Garrett, B. C.; Truhlar, D. G. J. Chem. Phys. 1980, 72, 3460.