A Pauson-Khand-type reaction between alkynes and olefinic aldehydes catalyzed by rhodium/cobalt heterobimetallic nanoparticles: An olefinic aldehyde as an olefin and CO source

Organic Letters

Volumn 6, Issue 7, 2004, Pages 1183-1186

  Park, Kang Hyun ^a   Jung, Il Gu ^a   Chung, Young Keun ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACROLEIN; ALDEHYDE; ALKENE; ALKYNE; CARBON MONOXIDE; CINNAMALDEHYDE; COBALT; CROTONALDEHYDE; RHODIUM;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; CYCLOADDITION; NANOTECHNOLOGY; PAUSON KHAND REACTION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 2342621283     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049765s     Document Type: Article

References (38)

1. (a) Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, 1998.
2. (b) Tundo, P.; Anastas, P. T. Green Chemistry: Challenging Perspectives; Oxford University Press: Oxford, 2000.
3. For recent reviews, see: (a) Gibson, S. E.; Stevenazzi, A. Angew. Chem., Int. Ed. 2003, 42, 1800. (b) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (c) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297.
4. For recent reviews, see: (a) Gibson, S. E.; Stevenazzi, A. Angew. Chem., Int. Ed. 2003, 42, 1800. (b) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (c) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297.
5. For recent reviews, see: (a) Gibson, S. E.; Stevenazzi, A. Angew. Chem., Int. Ed. 2003, 42, 1800. (b) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (c) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297.
6. (a) Morimoto, T.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. J. Am. Chem. Soc. 2002, 124, 3806.
7. (b) Shibata, T.; Toshida, N.; Takagi, K. Org. Lett. 2002, 4, 1619.
8. (c) Shibata, T.; Toshida, N.; Takagi, K. J. Org. Chem. 2002, 67, 7446.
9. (d) Park, K. H.; Son, S. U.; Chung, Y. K. Chem. Commun. 2003, 1898.
10. (a) Buchan, C.; Hamel, N.; Woell, J. B.; Alper, H. J. Chem. Soc., Chem. Commun. 1986, 167.
11. (b) Castanet, Y.; Mortreux, A.; Petit, F. J. Mol. Catal. 1990, 63, 313.
12. (c) Carpentier, J. P.; Castanet, Y.; Brocard, Y.; Mortreux, A.; Petit, F. Tetrahedron Lett. 1991, 32, 4705.
13. (d) Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750.
14. (e) Ko, S.; Lee, C.; Choi, M.-G.; Na, Y.; Chang, S. J. Org. Chem. 2003, 68, 1607.
15. (a) Kim, S.-W.; Son, S. U.; Chung, Y. K.; Hyeon, T. Chem. Commun. 2001, 2212.
16. (b) Son, S. U.; Lee, S. I.; Chung, Y. K.; Kim, S.-W.; Hyeon, T. Org. Lett. 2002, 4, 277.
17. (c) Son, S. U.; Park, K. H.; Chung, Y. K. J. Am. Chem. Soc. 2002, 124, 6838.
18. (d) Son, S. U.; Park, K. H.; Chung, Y. K. Org. Lett. 2002, 4, 3983.
19. (e) Park, K. H.; Son, S. U.; Chung, Y. K. Org. Lett. 2002, 4, 4361.
20. Park, K. H.; Kim, S. Y.; Chung, Y. K. J. Org. Chem. Submitted.
21. (a) Bohm, D.; Hamann, J.; Kripylo, P. J. Prak. Chem. 1990, 332, 710.
22. (b) Brown, N. F.; Barteau, M. A. J. Am. Chem. Soc. 1992, 114, 4258.
23. (c) Rupp, R.; Huttner, G.; Rutsch, P.; Winterhalter, U.; Barth, A.; Kircher, P.; Zsolnai, L. Eur. J. Inorg. Chem. 2000, 523.
24. See Supporting Information.
25. (a) Khand, I. U.; Mahaffy, C. A. L.; Pasuon, P. L. J. Chem. Res., Miniprint 1978, 4454.
26. (b) Krafft, M. E.; Romero, R. H.; Scott, I. L. J. Org. Chem. 1992, 57, 5277.
27. (a) Ahmar, M.; Antras, F.; Cazes, B. Tetrahedron Lett. 1999, 40, 5503.
28. (b) Rivero, M. R.; Adrio, J.; Carretero, C. Eur. J. Org. Chem. 2002, 2881.
29. (c) Rivero, M. R.; Carretero, J. C. J. Org. Chem. 2003, 68, 2975.
30. (a) de Jesus, J. C.; Zaera, F. J. Mol Catal. A: Chem. 1999, 138, 237.
31. (b) de Jesus, J. C.; Zaera, F. Surf. Sci. 1999, 430, 99.
32. Bock, H.; Breuer, O. Angew. Chem. 1987, 99, 492
33. Khand, I. U.; Pauson, P. L. J. Chem. Res., Synop. 1977, 9.
34. (a) Pauson, P. L.; Khand, I. U. Ann. N. Y. Acad. Sci. 1977, 295, 2.
35. (b) Khand, I. U.; Murphy, E.; Pasuon, P. L. J. Chem. Res., Synop. 1978, 350.
36. (c) Pauson, P. L. Tetrahedron 1985, 41, 5855.
37. Kang, Y. K.; Lee, H.-K.; Lee, S. S.; Chung, Y. K.; Carpenter, G. B. Inorg. Chim. Acta 1997, 261, 37.
38. Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 11492 and references therein.