Halide ions as a highly efficient promoter in the Ru-catalyzed hydroesterification of alkenes and alkynes

Organic Letters

Volumn 8, Issue 19, 2006, Pages 4355-4358

  Eun, Ju Park ^a   Ji, Min Lee ^a   Han, Hoon ^a   Chang, Sukbok ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33749003163     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061753e     Document Type: Article

References (50)

1. For selected examples of hydroacylation of alkenes, see: (a) Lochow, C. F.; Miller, R. G. J. Am. Chem. Soc. 1976, 98, 1281-1283.
2. (b) Marder, T. B.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451-1453.
3. (c) Bosnich, B. Acc. Chem. Res. 1998, 31, 667-674.
4. (d) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 11492-11493.
5. (e) Sato, Y.; Oonishi, Y.; Mori, M. Angew. Chem., Int. Ed. 2002, 41, 1218-1221.
6. (f) Tanaka, M.; Sakai, K.; Suemune, H. Curr. Org. Chem. 2003, 7, 353-367.
7. (g) Kakiuchi, F.; Chatani, N. Top. Organomet. Chem. 2004, 11, 45-79.
8. (a) Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750-751.
9. (b) Na, Y.; Ko, S.; Hwang, L. K.; Chang, S. Tetrahedron Lett. 2003, 44, 4475-4478.
10. (c) Ko, S.; Lee, C.; Choi, M.-G.; Na, Y.; Chang, S. J. Org. Chem. 2003, 68, 1607-1610.
11. (d) Ko, S.; Han, H.; Chang, S. Org. Lett. 2003, 5, 2687-2690.
12. For some selected examples, see: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529-531.
13. (b) Itami, K.; Koike, T.; Yoshida, J.-i. J. Am. Chem. Soc. 2001, 123, 6957-6958.
14. (c) Han, H.; Bae, I.; Yoo, E. J.; Lee, J.; Do, Y.; Chang, S. Org. Lett. 2004, 6, 4109-4112.
15. (d) Ko, S.; Kang, B.; Chang, S. Angew. Chem., Int. Ed. 2005, 44, 455-457.
16. For an intuitive mechanistic work on the hydroesterification of olefins using 1, see: (a) Wang, L.; Floreancig, P. E. Org. Lett. 2004, 6, 569-572.
17. (b) Wang, L.; Floreancig, P. E. Org. Lett. 2004, 6, 4207-4210.
18. For selected examples of halide additive effects in catalytic reactions, see: (a) Lavigne. G.; Kaesz, H. D. J. Am. Chem. Soc. 1984, 106, 4647-4648.
19. (b) Dombek, B. D. Organometallics, 1985, 4, 1707-1712.
20. (c) Kiso, Y.; Tanaka, M.; Nakamura, H.; Yamasaki, T.; Saeki, K. J. Organomet. Chem. 1986, 312, 357-364.
21. (d) Yoshida, S.-I.; Mori, S.; Kinoshita, H.; Watanabe, Y. J. Mol. Catal. 1987, 42, 215-227.
22. (e) Lautens, M.; Fagnou, K.; Yang, D. J. Am. Chem. Soc. 2003, 125, 14884-14892.
23. (f) Dahlén, A.; Hilmersson, G. Eur. J. Inorg. Chem. 2004, 3393-3403.
24. (g) Ruck, R. T.; Zuckerman, R. L.; Krska, S. W.; Bergman, R. G. Angew. Chem., Int. Ed. 2004, 43, 5375-5377.
25. For selected examples showing that the addition of certain salts to a solution of rutheniumcarbonyl complexes results in catalytically more active species, see: (a) Dombek, B. D. J. Am. Chem. Soc. 1981, 103, 6508-6510.
26. (b) Knifton, J. F. J. Am. Chem. Soc. 1981, 103, 3959-3961.
27. (c) Dombek, B. D. J. Organomet. Chem. 1983, 250, 467-483.
28. (d) Dombek, B. D. J. Organomet. Chem. 1989, 372, 151-161.
29. (e) Lavigne, G. Eur. J. Inorg. Chem. 1999, 917-930.
30. (f) Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 26-47.
31. 11] could be used as a good catalyst precursor in the hydroesterification of ethylene using methyl formate at 160°C: (a) Lavigne, G.; Lugan, N.; Kalck, P.; Soulié, J. M.; Lerouge, O.; Saillard, J. Y.; Halet, J. F. J. Am. Chem. Soc. 1992, 114, 10669-10670.
32. (b) Lugan, N.; Lavigne, G.; Soulié, J. M.; Fabre, S.; Kalck, P.; Saillard, J. Y.; Halet, J. F. Organometallics 1995, 14, 1712-1731.
33. 12 catalysis, see: (a) Tokunaga, M.; Eckert, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 1999, 38, 3222-3225.
34. (b) Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 6646-6647.
35. (c) Yi, C. S.; Yun, S. Y.; Guzei, I. A. J. Am. Chem. Soc. 2005, 127, 5782-5783.
36. (a) Han, S.-H.; Geoffroy, G. L.; Dombek, B. D.; Rheingold, A. L. Inorg. Chem. 1988, 27, 4355-4361.
37. (b) Rivomanana. S.; Lavigne. G.; Lugan, N.; Bonnet. J.-J. Organometalllics 1991, 10, 2285-2297.
38. (a) Bor, G. Pure Appl. Chem. 1986, 58, 543-552.
39. (b) Koelliker, R.; Bor, G. J. Organomet. Chem. 1991, 417, 439-451.
40. See the Supporting Information for details.
41. 12-catalyzed reactions. Hydrogenation of carbon dioxide: (a) Tominaga, K.-i.; Sasaki, Y. J. Mol. Catal. A: Chem. 2004, 220, 159-165.
42. Oxonation of olefins: (b) Knifton, J. F. J. Mol. Catal. 1988, 47, 99-116.
43. Alkoxycarbonylation: (c) Hidai, M.; Koyasu, Y.; Chikanari, K.; Uchida, Y. J. Mol. Catal. 1987, 40, 243-254.
44. 2: (d) Keister, J. B.; Gentile, R. J. Organomet. Chem. 1981, 222, 143-153.
45. Homologation of methyl formate: (e) Ragaini, F.; Cenini, S. J. Mol. Catal. A: Chem. 2000, 161, 31-38.
46. Reductive carbonylation of aromatic nitro compounds: (f) Pizzotti, M.; Cenini, S.; Quici, S.; Tollari, S. J. Chem. Soc., Perkin Trans. 2. 1994, 913-917.
47. (a) Ayllon, J. A.; Sayers, S. F.; Sabo-Etienne, S.; Donnadieu, B.; Chaudret, B.; Clot, E. Organometallics 1999, 18, 3981-3990.
48. (b) Grumbine, S. K.; Mitchell, G. P.; Straus, D. A.; Tilley, T. D.; Rheingold, A. L. Organometallics 1998, 17, 5607-5619.
49. (c) Na, Y.; Chang, S. Org. Lett. 2000, 2, 1887-1889.
50. (d) Lee, M.; Ko, S.; Chang, S. J. Am. Chem. Soc. 2000, 122, 12011-12012.