Remarkable improvement achieved by imidazole derivatives in ruthenium-catalyzed hydroesterification of alkenes using formates

Organic Letters

Volumn 14, Issue 18, 2012, Pages 4722-4725

  Konishi, Hideyuki ^a   Ueda, Tsuyoshi ^b   Muto, Takashi ^a   Manabe, Kei ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; FORMIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; LIGAND; RUTHENIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ALKENES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; FORMATES; IMIDAZOLES; LIGANDS; MOLECULAR STRUCTURE; RUTHENIUM COMPOUNDS;

EID: 84868216983     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301850y     Document Type: Article

References (36)

1. (a) El Ali, B.; Alper, H. Hydrocarboxylation and hydroesterification reactions catalyzed by transition metal complexes. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH:Weinheim, 2004; pp 113-132.
2. (b) Brennfuehrer, A.; Neumann, H.; Beller, M. ChemCatChem 2009, 1, 28-41.
3. Kiss, G. Chem. Rev. 2001, 101, 3435-3456.
4. (a) Morimoto, T.; Kakiuchi, K. Angew. Chem., Int. Ed. 2004, 43, 5580-5588.
5. (b) Keim, W. Pure Appl. Chem. 1986, 58, 825-832.
6. (a) Isnard, P.; Denise, B.; Sneeden, R. P. A. J. Organomet. Chem. 1983, 256, 135-139.
7. (b) Mlekuz, M.; Joo, F.; Alper, H. Organometallics 1987, 6, 1591-1593.
8. (c) Ueda, W.; Yokoyama, T.; Morikawa, Y.; Moro-oka, Y.; Ikawa, T. J. Mol. Catal. 1988, 44, 197-200.
9. (d) Kondo, T.; Yoshii, S.; Tsuji, Y.; Watanabe, Y. J. Mol. Catal. 1989, 50, 31-38.
10. (e) Keim, W.; Becker, J. J. Mol. Catal. 1989, 54, 95-101.
11. (f) Lin, I. J. B.; Alper, H. J. Chem. Soc., Chem. Commun. 1989, 248-249.
12. (g) Nahmed, E. M.; Jenner, G. J. Mol. Catal. 1990, 59, L15-L19.
13. (h) Grévin, J.; Kalck, P. J. Organomet. Chem. 1994, 476, C23-C24.
14. (i) Legrand, C.; Castanet, Y.; Mortreux, A.; Petit, F. J. Chem. Soc., Chem. Commun. 1994, 1173-1174.
15. (j) Suzuki, Y.; Katoh, H.; Ishii, Y.; Hidai, M. J. Mol. Catal. A 1995, 95, 129-133.
16. (k) Lugan, N.; Lavigne, G.; Soulié, J. M.; Fabre, S.; Kalck, P.; Saillard, J. Y.; Halet, J. F. Organometallics 1995, 14, 1712-1731.
17. (l) Fabre, S.; Kalck, P.; Lavigne, G. Angew. Chem., Int. Ed. 1997, 36, 1092-1095.
18. (m) Kondo, T.; Okada, T.; Mitsudo, T. Organometallics 1999, 18, 4123-4127.
19. For use of methyl formate, see review: (a) Jenner, G. Appl. Catal., A 1995, 121, 25-44. For a recent example, see
20. (b) Lee, H. W.; Chan, A. S. C.; Kwong, F. Y. Chem. Commun. 2007, 2633-2635.
21. (a) Trost, B. M. Science 1991, 254, 1471-147.
22. (b) Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705.
23. Both decarbonylation and decarboxylation of alkyl formates have been reported: (a) Kondo, T.; Tantayanon, S.; Tsuji, Y.; Watanabe, Y. Tetrahedron Lett. 1989, 30, 4137-4140.
24. (b) Jenner, G.; Nahmed, E. M.; Leismann, H. Tetrahedron Lett. 1989, 30, 6501-6502.
25. (c) Vega, F. R.; Clément, J.-C.; des Abbayes, H. Tetrahedron Lett. 1993, 34, 8117-8118.
26. (a) Mlekuz, M.; Joo, F.; Alper, H. Organometallics 1987, 7, 1591-1593.
27. (b) Kondo, T.; Yoshii, S.; Tsuji, Y.; Watanabe, Y. J. Mol. Catal. 1989, 50, 31-38.
28. (c) Lin, I. J. B.; Alper, H. J. Chem. Soc., Chem. Commun. 1989, 248-249.
29. (d) Suzuki, Y.; Katoh, H.; Ishii, Y.; Hidai, M. J. Mol. Catal. A 1995, 95, 129-133.
30. (a) Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750-751.
31. (b) Na, Y.; Ko, S.; Hwang, L. K.; Chang, S. Tetrahedron Lett. 2003, 44, 4475-4478.
32. Katafuchi, Y.; Fujihara, T.; Iwai, T.; Terao, J.; Tsuji, Y. Adv. Synth. Catal. 2011, 353, 475-482.
33. Wang, L.; Floreancig, P. E. Org. Lett. 2004, 6, 4207-4210.
34. Jenner, G.; Nahmed, E. M.; Leismann, H. J. Organomet. Chem. 1990, 387, 315-321.
35. (a) Dallmann, K.; Buffon, R. J. Mol. Catal. A 2001, 172, 81-87.
36. (b) Ammar, H. B.;Nôtre, J. L.; Salem, M.; Kaddachi, M. T.; Toupet, L.; Renaud, J.-L.; Bruneau, C.; Dixneuf, P. H. Eur. J. Inorg. Chem. 2003, 4055-4064.