Palladium-catalyzed asymmetric arylation of 2,3-dihydrofuran with aryl triflates in water in the presence of surfactants

Journal of Molecular Catalysis A: Chemical

Volumn 215, Issue 1-2, 2004, Pages 89-93

  Rabeyrin, Cedric ^a   Sinou, Denis ^a  

^a CPE LYON   (France)

Author keywords

Aqueous micelles; Asymmetric arylation; Palladium

Indexed keywords

CATALYST ACTIVITY; ORGANOMETALLICS; PALLADIUM; SURFACE ACTIVE AGENTS; WATER;

ARYL TRIFLATES; BINAP; ENANTIOMERIC EXCESS; MILD CONDITIONS;

CATALYSIS;

2,3 DIHYDROFURAN; FURAN DERIVATIVE; PALLADIUM COMPLEX; SURFACTANT; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; ARYLATION; CATALYST; CHEMICAL ANALYSIS; CHIRALITY; ENANTIOMER; MICELLE; REACTION ANALYSIS; SURFACE PROPERTY;

EID: 1942436180     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2004.01.021     Document Type: Article

References (52)

1. B. Cornils, W.A. Herrmann (Eds.), Applied Homogeneous Catalysis with Organometallic Compounds, Wiley-VCH, Weinheim, 1996.
2. M. Beller, C. Bolm (Eds.), Transition Metals for Organic Synthesis, Wiley-VCH, Weinheim, 1998.
3. B. Cornils, W.A. Herrmann (Eds.), Aqueous-Phase Organometallic Chemistry. Concepts and Applications, Wiley-VCH, Weinheim, 1996.
4. Cornils B. Angew. Chem. Int. Ed. Engl. 34:1995;1575.
5. Sinou D. Top. Curr. Chem. 206:1999;41.
6. Sinou D. Adv. Synth. Catal. 344:2002;221.
7. Welton T. Chem. Rev. 99:1999;2071.
8. Wasserscheidt P., Keim W. Angew. Chem. Int. Ed. Engl. 39:2000;3772.
9. P.G. Jessop, W. Leitner (Eds.), Chemical Synthesis in Supercritical Fluids, Wiley-VCH, New York, 1999.
10. Horvàth I.T., Ràbai J. Science. 266:1994;72.
11. Oehme G., Paetzold E., Selke R. J. Mol. Catal. 71:1992;L1.
12. Grassert I., Paetzold E., Oehme G. Tetrahedron. 49:1993;6605.
13. Grassert I., Vill V., Oehme G. J. Mol. Catal. A: Chem. 116:1997;231.
14. Grassert I., Schmidt U., Ziegler S., Fischer C., Oehme G. Tetrahedron: Asymmetry. 9:1998;4193.
15. Oehme G., Grassert I., Ziegler S., Meisel R., Fuhrmann H. Catal. Today. 42:1998;459.
16. Dwars T., Schmidt U., Fischer C., Grassert I., Kempe R., Fröhlich R., Drauz K., Oehme G. Angew. Chem. Int. Ed. 37:1998;2851.
17. Selke R., Holz J., Riepe A., Börner A. Chem. Eur. J. 4:1998;769.
18. Trinkhaus S., Kadyrov R., Selke R., Holz J., Götze L., Börner A. J. Mol. Catal. A: Chem. 144:1999;15.
19. Oehme G., Grassert I., Paetzold E., Meisel R., Drexler K., Fuhrmann H. Coord. Chem. Rev. 185-186:1999;585.
20. Robert F., Oehme G., Grassert I., Sinou D. J. Mol. Catal. A: Chem. 156:2000;127.
21. Dwars T., Haberland J., Grassert I., Oehme G., Kragl U. J. Mol. Catal. A: Chem. 168:2001;81.
22. Ding H., Hanson B.E., Bakos J. Angew. Chem. Int. Ed. Engl. 34:1995;1645.
23. Grassert I., Kovàcs J., Fuhrmann H., Oehme G. Adv. Synth. Catal. 344:2002;312.
24. Goedheijt M.S., Hanson B.E., Reek J.N.H., Kamer P.C.J., van Leeuwen P.W.N.M. J. Am. Chem. Soc. 122:2000;1650.
25. Chen H., Li Y., Chen J., Cheng P., He Y., Li X. J. Mol. Catal. A: Chem. 149:1999;1.
26. Uozumi Y., Danjo H., Hayashi T. Tetrahedron Lett. 38:1997;3557.
27. Uozumi Y., Danjo H., Hayashi T. Tetrahedron Lett. 39:1998;8303.
28. Uozumi Y., Shibatomi K. J. Am. Chem. Soc. 123:2001;2919.
29. Rabeyrin C., Nguefack C., Sinou D. Tetrahedron Lett. 41:2000;7461.
30. Sinou D., Nguefack C., Rabeyrin C. Adv. Synth. Catal. 345:2003;357.
31. Rabeyrin C., Sinou D. Tetrahedron: Asymmetry. 14:2003;3891.
32. Kobayashi S., Lam W.W.-L., Manabe K. Tetrahedron Lett. 41:2000;6115.
33. Paetzold E., Oehme G. J. Mol. Catal. A: Chem. 152:2000;69.
34. Badone D., Baroni M., Cardamone R., Ielmini A., Guzzi U. J. Org. Chem. 62:1997;7170.
35. Bumagin N.A., Bykov V.V., Sukhomlinova L.L., Tolstaya T.P., Beletskaya I.P. J. Organomet. Chem. 486:1995;259.
36. Cheprakov A.V., Ponomareva N.V., Beletskaya I.P. J. Organomet. Chem. 486:1995;297.
37. Manabe K., Mori Y., Wakabayashi T., Nagayama S., Kobayashi S. J. Am. Chem. Soc. 122:2000;7202.
38. de Meijere A., Meyer F.E. Angew. Chem. Int. Ed. Engl. 33:1994;2379.
39. Cabri W., Candiani I. Acc. Chem. Res. 28:1995;2.
40. T. Jeffery, in: L.S. Liebeskind (Ed.), Advances in Metal-Organic Chemistry, vol. 5, JAI Press, Greenwich, 1996, pp. 153-260.
41. Ozawa F., Kobatake Y., Hayashi T. Tetrahedron Lett. 34:1993;2505.
42. Ozawa F., Kubo A., Hayashi T. J. Am. Chem. Soc. 113:1991;1417.
43. Ozawa F., Kubo A., Hayashi T. Tetrahedron Lett. 33:1992;1485.
44. Ozawa F., Kubo A., Matsumoto Y., Hayashi T., Nishioka E., Yanagi K., Moriguchi K.-I. Organometallics. 12:1993;4188.
45. Koga Y., Sodeoka M., Shibasaki M. Tetrahedron Lett. 35:1994;1227.
46. Loiseleur O., Meier P., Pfaltz A. Angew. Chem. Int. Ed. Engl. 35:1996;200.
47. Loiseleur O., Hayashi M., Keenan M., Schmees N., Pfaltz A. J. Organomet. Chem. 576:1999;16.
48. Flubacher D., Helmchen G. Tetrahedron Lett. 40:1999;3867.
49. Jeffery T. Tetrahedron Lett. 35:1994;3051.
50. Jeffery T. Tetrahedron. 52:1996;10113.
51. Cabri W., Candiani I., Bedeschi A., Penco S. J. Org. Chem. 57:1992;1481.
52. Echavarren A.M., Stille J.K. J. Am. Chem. Soc. 109:1987;5478.