New amphiphilic palladium-phosphine complexes bound to solid supports: Preparation and use for catalytic allylic substitution in aqueous media

Tetrahedron Letters

Volumn 38, Issue 20, 1997, Pages 3557-3560

  Uozumi, Yasuhiro ^a   Danjo, Hiroshi ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030922520     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00702-8     Document Type: Article

References (24)

1. For a review: Tsuji, J. "Palladium Reagents and Catalysts", John Wiley and Sons: Chichester, 1995.
2. For a review: Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544.
3. For recent examples of reactions catalyzed by palladium-phosphine complexes performed in aqueous media: (a) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717.
4. (b) Genêt, J. P.; Blart, E.; Savignac, M.; Lemeune, S.; Paris, J.-M. Tetrahedron Lett. 1993, 34, 4189-4192.
5. (c) Lemaire-Audoire, S.; Savignac, M.; Blart, E.; Pourcelot, G.; Genêt, J. P. Tetrahedron Lett. 1994, 35, 8783-8786.
6. (d) Genêt, J. P.; Blart, E.; Savignac, M.; Lemeune, S.; Lemaire-Audoire, S.; Paris, J.-M.; Bernard, J.-M. Tetrahedron 1994, 50, 497-503.
7. (e) Blart, E.; Genêt, J. P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505-514.
8. (f) Amatore, C.; Blart, E.; Genêt, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829-6839.
9. (g) Lemaire-Audoire, S.; Savignac, M.; Dupuis, C.; Genêt, J. P. Tetrahedron Lett. 1996, 37, 2003-2006.
10. (h) Bumagin, N. A.; Bykov, V. V.; Sukhomlinova, L. I.; Tolstaya, T. P.; Beletskaya, I. P. J. Organomet. Chem. 1995, 486, 259-262.
11. For recent examples of preparation of transition metal-phosphine complexes on solid supports: (a) Gilbertson, S. R.; Wang, X.; Hoge, G. S.; Klug, C. A.; Schaefer, J. Organometallics 1996, 15, 4678-4680.
12. (b) Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475-6478.
13. (a) Bayer, E.; Rapp, W. Chemistry of Peptides and Proteins; Voelter, W.; Bayer, E.; Ovchinikov, Y. A.; Iwanov, V. T. Eds.; Walter de Gruter, Berlin, 1986; Vol. 3, pp 3-8.
14. (b) Rapp, W. In Combinatorial Peptide and Nonpeptide Libraries; Jung, G. Ed.; VCH, Weilheim, 1996; pp 425-464.
15. 2 (130 μm of diameter) was purchased from Rapp Polymere, Germany and washed with acetonitrile and dichloromethane before use.
16. EDCI= 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. HOBt= 1-hydroxybenzotriazole hydrate.
17. Johnson, C. R.; Zhang, B. Tetrahedron Lett. 1995, 36, 9253-9256.
18. 31P NMR: δ +25.9 ppm.
19. 3 as a base in an organic solvent (e.g. THF, dioxane, or toluene) where much higher reaction temperature is required than the temperature in the reaction catalyzed by 3 in water. For example: Gravel, D.; Benoit, S.; Kumanovic, S.; Sivaramakrishnan, H. Tetrahedron Lett. 1992, 33, 1407-1410.
20. 3 (Pd/P = 1/2) and DBU as a base in THF gave 6% yield of 7a at room temperature.
21. TPPTS = triphenylphosphinetrisulfonate sodium salt. Sinou, D. Bull. Soc. Chim. Fr. 1987, 3, 480-486. See also ref 3a-g.
22. Inomata, K.; Yamamoto, T.; Kotake, H. Chem. Lett. 1981, 1357-1360.
23. Murahashi, S.-I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292-3303.
24. 4 and chromatographed on silica gel to give 7a. The recovered catalyst was dried under reduced pressure for 30 min and then used in the next reaction under the same reaction conditions.