Double phosphinylation of propargylic alcohols: A novel synthetic route to 1,2-bis(diphenylphosphino)ethane derivatives

Organic Letters

Volumn 6, Issue 22, 2004, Pages 3993-3995

  Milton, Marilyn Daisy ^a   Onodera, Gen ^a   Nishibayashi, Yoshiaki ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BIS(DIPHENYLPHOSPHINO)ETHANE; ALCOHOL DERIVATIVE; ETHANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 8844251507     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048347k     Document Type: Article

References (28)

1. (a) Nishibayashi, Y.; Wakiji, I.; Hidai, M. J. Am. Chem. Soc. 2000, 122, 11019.
2. (b) Nishibayashi, Y.; Onodera, G.; Inada, Y.; Hidai, M.; Uemura, S. Organometallics 2003, 22, 873.
3. (c) Nishibayashi, Y.; Imajima, H.; Onodera, G.; Hidai, M.; Uemura, S. Organometallics 2004, 23, 26.
4. (d) Nishibayashi, Y.; Yoshikawa, M.; Inada, Y.; Hidai, M.; Uemura, S. J. Org. Chem. 2004, 69, 3408.
5. (a) The thiolate-bridged diruthenium complexes (1) were found to provide an unique bimetallic reaction site for activation and transformation of various terminal alkynes; see: Nishibayashi, Y.; Yamanashi, M.; Wakiji, I.; Hidai, M. Angew. Chem., Int. Ed. 2000, 39, 2909 and references therein.
6. 2-RuCp*Cl] (1a) is commercially available from Wako Pure Chemical Industries (Japan) as met-DIRUX (methanethiolate-bridged diruthenium complex) (130-14581).
7. Nishibayashi, Y.; Milton, M. D.; Inada, Y.; Yoshikawa, M.; Wakiji, I.; Hidai, M.; Uemura, S. Chem. Eur. J., in press.
8. ,2-Bis(diphenylphosphino)ethane (dppe) has been used as a typical bidentate ligand for various transition metals, see some recent examples: (a) Arisawa, M.; Yamaguchi, M J. Am. Chem. Soc. 2003, 125, 6624. (b) Maleczka, R. E.; Shi, F.; Holmes, D.; Smith, M. R. J. Am. Chem. Soc. 2003, 125, 7792. (c) Kuwano, R.; Kondo, Y.; Matsuyama, Y. J. Am. Chem. Soc. 2003, 125, 12104.
9. ,2-Bis(diphenylphosphino)ethane (dppe) has been used as a typical bidentate ligand for various transition metals, see some recent examples: (a) Arisawa, M.; Yamaguchi, M J. Am. Chem. Soc. 2003, 125, 6624. (b) Maleczka, R. E.; Shi, F.; Holmes, D.; Smith, M. R. J. Am. Chem. Soc. 2003, 125, 7792. (c) Kuwano, R.; Kondo, Y.; Matsuyama, Y. J. Am. Chem. Soc. 2003, 125, 12104.
10. ,2-Bis(diphenylphosphino)ethane (dppe) has been used as a typical bidentate ligand for various transition metals, see some recent examples: (a) Arisawa, M.; Yamaguchi, M J. Am. Chem. Soc. 2003, 125, 6624. (b) Maleczka, R. E.; Shi, F.; Holmes, D.; Smith, M. R. J. Am. Chem. Soc. 2003, 125, 7792. (c) Kuwano, R.; Kondo, Y.; Matsuyama, Y. J. Am. Chem. Soc. 2003, 125, 12104.
11. 17OP [M] 316.1017, found 316.1015.
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13. (b) Pravia, K.; White, R.; Fodda, R.; Maynard, D. F. J. Org. Chem. 1996, 61, 6031.
14. Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
15. Some recent examples: (a) Han, L.-B.; Zhang, C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080. (b) Jérôme, F.; Monnier, F.; Lawicka, H.; Dérien, S.; Dixneuf, P. H. Chem. Commun. 2003, 696. (c) Depréle, S.; Montchamp, J.-L. J. Am. Chem. Soc. 2002, 124, 9386. (d) Han, L.-B.; Zhao, C.-Q.; Tanaka, M. J. Org. Chem. 2001, 66, 5929 (e) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc. 2000, 122, 5407. (f) Han, L.-B.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (g) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
16. Some recent examples: (a) Han, L.-B.; Zhang, C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080. (b) Jérôme, F.; Monnier, F.; Lawicka, H.; Dérien, S.; Dixneuf, P. H. Chem. Commun. 2003, 696. (c) Depréle, S.; Montchamp, J.-L. J. Am. Chem. Soc. 2002, 124, 9386. (d) Han, L.-B.; Zhao, C.-Q.; Tanaka, M. J. Org. Chem. 2001, 66, 5929 (e) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc. 2000, 122, 5407. (f) Han, L.-B.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (g) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
17. Some recent examples: (a) Han, L.-B.; Zhang, C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080. (b) Jérôme, F.; Monnier, F.; Lawicka, H.; Dérien, S.; Dixneuf, P. H. Chem. Commun. 2003, 696. (c) Depréle, S.; Montchamp, J.-L. J. Am. Chem. Soc. 2002, 124, 9386. (d) Han, L.-B.; Zhao, C.-Q.; Tanaka, M. J. Org. Chem. 2001, 66, 5929 (e) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc. 2000, 122, 5407. (f) Han, L.-B.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (g) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
18. Some recent examples: (a) Han, L.-B.; Zhang, C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080. (b) Jérôme, F.; Monnier, F.; Lawicka, H.; Dérien, S.; Dixneuf, P. H. Chem. Commun. 2003, 696. (c) Depréle, S.; Montchamp, J.-L. J. Am. Chem. Soc. 2002, 124, 9386. (d) Han, L.-B.; Zhao, C.-Q.; Tanaka, M. J. Org. Chem. 2001, 66, 5929 (e) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc. 2000, 122, 5407. (f) Han, L.-B.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (g) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
19. Some recent examples: (a) Han, L.-B.; Zhang, C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080. (b) Jérôme, F.; Monnier, F.; Lawicka, H.; Dérien, S.; Dixneuf, P. H. Chem. Commun. 2003, 696. (c) Depréle, S.; Montchamp, J.-L. J. Am. Chem. Soc. 2002, 124, 9386. (d) Han, L.-B.; Zhao, C.-Q.; Tanaka, M. J. Org. Chem. 2001, 66, 5929 (e) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc. 2000, 122, 5407. (f) Han, L.-B.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (g) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
20. Some recent examples: (a) Han, L.-B.; Zhang, C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080. (b) Jérôme, F.; Monnier, F.; Lawicka, H.; Dérien, S.; Dixneuf, P. H. Chem. Commun. 2003, 696. (c) Depréle, S.; Montchamp, J.-L. J. Am. Chem. Soc. 2002, 124, 9386. (d) Han, L.-B.; Zhao, C.-Q.; Tanaka, M. J. Org. Chem. 2001, 66, 5929 (e) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc. 2000, 122, 5407. (f) Han, L.-B.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (g) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
21. Some recent examples: (a) Han, L.-B.; Zhang, C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080. (b) Jérôme, F.; Monnier, F.; Lawicka, H.; Dérien, S.; Dixneuf, P. H. Chem. Commun. 2003, 696. (c) Depréle, S.; Montchamp, J.-L. J. Am. Chem. Soc. 2002, 124, 9386. (d) Han, L.-B.; Zhao, C.-Q.; Tanaka, M. J. Org. Chem. 2001, 66, 5929 (e) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc. 2000, 122, 5407. (f) Han, L.-B.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259. (g) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
22. (a) Palladium-catalyzed bisphosphorylation of alkynes with dialkyl phosphites to give the corresponding 1,2-bisphosphonates has been reported: Allen, A., Jr.; Manke, D. R.; Lin, W. Tetrahedron Lett. 2000, 41, 151.
23. (b) Palladium-catalyzed bisphosphinylation of alkynes with diphenylphosphine oxide to give the corresponding 1,2-bisphosphine oxides has been reported: Allen, A., Jr.; Ma, L.; Lin, W. Tetrahedron Lett. 2002, 43, 3707.
24. A related Ni-catalyzed phosphinylation of propargylic alcohols with diphenylphosphine oxide to give the corresponding phosphoroyl-substituted 1,3-butadienes has been reported; Han, L.-B.; Yazawa, H. The 84th Annual Meeting of the Chemical Society of Japan, Kobe, March 2004, Abstract 3PC-193.
25. Chiraphos (2,3-bis(diphenylphosphinyl)butane) has been widely used as a chiral bidentate ligand for various transition metals. For some recent examples, see: (a) Kimmich, B. F. M.; Somsook, E.; Landis, C. R. J. Am. Chem. Soc. 1998, 120, 10115. (b) Wicht, D. K.; Zhuravel, M. A.; Gregush, R. V.; Glueck, D. S.; Guzei, I. A.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 1998, 17, 1412. (c) Casado, M. A.; Perez-Torrente, J. J.; Ciriano, M. A.; Oro, L. A.; Orejon, A.; Claver, C. Organometallics 1999, 18, 3035. (d) Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614.
26. Chiraphos (2,3-bis(diphenylphosphinyl)butane) has been widely used as a chiral bidentate ligand for various transition metals. For some recent examples, see: (a) Kimmich, B. F. M.; Somsook, E.; Landis, C. R. J. Am. Chem. Soc. 1998, 120, 10115. (b) Wicht, D. K.; Zhuravel, M. A.; Gregush, R. V.; Glueck, D. S.; Guzei, I. A.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 1998, 17, 1412. (c) Casado, M. A.; Perez-Torrente, J. J.; Ciriano, M. A.; Oro, L. A.; Orejon, A.; Claver, C. Organometallics 1999, 18, 3035. (d) Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614.
27. Chiraphos (2,3-bis(diphenylphosphinyl)butane) has been widely used as a chiral bidentate ligand for various transition metals. For some recent examples, see: (a) Kimmich, B. F. M.; Somsook, E.; Landis, C. R. J. Am. Chem. Soc. 1998, 120, 10115. (b) Wicht, D. K.; Zhuravel, M. A.; Gregush, R. V.; Glueck, D. S.; Guzei, I. A.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 1998, 17, 1412. (c) Casado, M. A.; Perez-Torrente, J. J.; Ciriano, M. A.; Oro, L. A.; Orejon, A.; Claver, C. Organometallics 1999, 18, 3035. (d) Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614.
28. Chiraphos (2,3-bis(diphenylphosphinyl)butane) has been widely used as a chiral bidentate ligand for various transition metals. For some recent examples, see: (a) Kimmich, B. F. M.; Somsook, E.; Landis, C. R. J. Am. Chem. Soc. 1998, 120, 10115. (b) Wicht, D. K.; Zhuravel, M. A.; Gregush, R. V.; Glueck, D. S.; Guzei, I. A.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 1998, 17, 1412. (c) Casado, M. A.; Perez-Torrente, J. J.; Ciriano, M. A.; Oro, L. A.; Orejon, A.; Claver, C. Organometallics 1999, 18, 3035. (d) Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614.