Building molecular complexity via tandem ru-catalyzed isomerization/C-H activation

Organic Letters

Volumn 11, Issue 8, 2009, Pages 1749-1752

  Bartoszewicz, Agnieszka ^a   Martín Matute, Belén ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 65249164233     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900243x     Document Type: Article

References (33)

1. Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705.
2. (a) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995.
3. (b) Metal-catahzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
4. (c) Brandsma, L.; Vaselevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1998.
5. (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda. M.; Chatani. N. Nature 1993, 366, 529-531. For a review, see:
6. (b) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826-834.
7. (c) Murai, S.; Kakiuchi, F.; Sekine. S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure App. Chem. 1994, 66, 1527-1534,
8. For reviews using Ru complexes, see: (a) Park. Y. J.; Jun, C.-H. Bull. Korean Chem. Soc. 2005, 26, 871-877.
9. (b) Kakiuchi. F.: Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101.
10. (c) Ritleng, V.; Sirlin, C; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1770.
11. (d) Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013-3039. For other metals, see:
12. (e) Ackermann, L. Top. Organomet. Chem. 2007, 24. 35-60.
13. (f) Satoh, T.; Miura. M. Top. Organomet. Chem. 2007, 24, 61-84.
14. (g) Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200-205.
15. (h) Alberico, D.; Scott. M. E.; Lautens. M. Chem. Rev. 2007, 107, 174- 238.
16. (i) Seregin, 1. V.; Gevorgyan. V. 'chem. Soc. Rev. 2007, 36, 1173- 1193.
17. (j) Bergman, R. G. Nature 2007, 446, 391-393.
18. (k) Campeau. L.-C; Stuart. D. R.; Fagnou, K. Aldrichim. Acta 2007, 40, 35-41.
19. (a) Martinez, R.; Chevalier, R.; Darses, S.; Genêt, J.-P. Angew. Chem., Int. Ed. 2006, 45, 8232-8235.
20. (b) Martinez, R.; Genet, J.-P.; Darses, S. Chem. Commun. 2008, 3855-3857.
21. (c) Simon, M. C; Martinez, R.; Genet, J.-P.; Darses, S. Adpv Synth. Catal. 2009, 351, 153-157.
22. Folev, N. A.; Ke. Z.; Gunnoe, T. B.; Cundari, T. R.; Petersen, J. L. Orsanometallics 2008, 27, 3007-3017.
23. Bartoszewicz, A.; Livendahl. M.; Martin-Matute. B. Chem.-Eur. J 42008, 14, 10547-10550.
24. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikai'iya, T.; Novori, R. J. Am. Chem, Soc. 1996, 118, 2521-2522.
25. Jardine, F. H. Prog. Inorg. Chem. 1984, 31, 265-370.
26. Although the reaction times for the isomerization/C-H activation did not change much in the presence of electron rich-phosphines, when only C-H activation from propiophenone was studied, the reaction time was decreased by a factor of 2. See Supporting Information.
27. 13C content (see Supporting Information).
28. 3 reacts with isopropanol to produce the corresponding dihydride, see: Aranyos, A.; Gsjemyik, G.; Szabó, K. J.; Bäckvall, J.-E. J. Chem. Soc, Chem. Commun. 1999, 351-352.
29. For a similar mechanistic studv using Ni complexes, see: Cuperlv. D.; Petrignet, J.; Crévisy, C; Grée, R. Chem.-Eur. J. 2006, 12, 3261- 3274. See also scheme in Supporting Information.
30. See crude NMR spectra in Supporting Information.
31. Theoretical studv of the mechanism, see: Matsubara, T.; Koga. N.; Musaev, D. G.: Morokuma. K. J Am. Chem. Soc. 1998, 120. 12692-12693.
32. For direct arylations widiout involving Ru(0) species, see: (a) Özdemir, I.; Demir. S.; Çetinkava. B.; Gourlaouen, C; Maseras. F.; Bruneau. C.; Dixneuf. P. H. J Am. Chem. Soc. 2008, 130, 1156-1157.
33. (b) Ackermann, L.; Vicente, R.; Althammer, A. Org. Lett. 2009, 102, 2299-2302.