Efficient synthesis of trisubstituted alkenes in an aqueous-organic system using a versatile and recyclable Rh/m-TPPTC catalyst

Tetrahedron Letters

Volumn 45, Issue 21, 2004, Pages 4157-4161

  Genin, Emilie ^a   Michelet, Véronique ^a   Genêt, Jean Pierre ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

Alkynes; Biphasic system; Boronic acids; Recyclable rhodium m TPPTC system; Water soluble ligand

Indexed keywords

ALKENE DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; ARYLATION; CATALYSIS; SILYLATION; SOLUBILITY; SYNTHESIS;

GADUS MORHUA;

EID: 2342563184     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.136     Document Type: Article

References (40)

1. For selected books, see: Grieco P.A. Organic Synthesis in Water. 1998;Blacky Academic and Professional, London
2. Li C.-J., Chan T.-H. Organic Reactions in Aqueous Media. 1997;Wiley & Sons, New York
3. Cornils B., Herrmann W.A. Aqueous-Phase Organometallic Catalysis. 1998;Wiley-VCH, New York
4. For recent reviews, see: Pinault N., Bruce D.W. Coord. Chem. Rev. 241:2003;1
5. Li C.-J. Acc. Chem. Res. 35:2002;533
6. Li C.-J., Chan T.H. Tetrahedron. 55:1999;11149
7. Lubineau A., Augé J. Knochel P. Modern Solvent in Organic Synthesis, Topics in Current Chemistry. 206:1999;1 Springer, Berlin
8. Sinou D. Knochel P. Modern Solvent in Organic Synthesis, Topics in Current Chemistry. 206:1999;41 Springer, Berlin
9. Lubineau A., Augé J., Queneau Y. Synthesis. 1994;741
10. Herrmann W.A., Kohlpaintner C.W. Angew. Chem., Int. Ed. Engl. 32:1993;1524
11. Michelet, V.; Savignac, M.; Genêt, J. P. Electronic Encyclopedia of Reagents for Organic Synthesis, in press
12. Genêt J.P., Savignac M. J. Organomet. Chem. 576:1999;305
13. Genêt J.P., Savignac M., Lemaire-Audoire S. IUPAC Monographs 'Chemistry for the 21st Century' Murahashi S.-I., Davies S.G. Transition Metal Catalyzed Reactions. 1999;55
14. Amengual R., Genin E., Michelet V., Savignac M., Genet J.P. Adv. Synth. Catal. 344:2002;393
15. Amengual R., Michelet V., Genêt J.P. Tetrahedron Lett. 43:2002;5905
16. Abbreviations: TPPTS = trisodium salt of 3, 3′, 3″-phosphanetriylbenzenesulfonic acid, TPPTC = trilithium salt of 3, 3′, 3″-phosphanetriylbenzenecarboxylic acid, TPPDS = dipotassium salt of 3, 3′-phosphanediylbenzenesulfonic acid
17. Hayashi T., Yamasaki K. Chem. Rev. 103:2003;2829
18. Fagnou K., Lautens M. Chem. Rev. 103:2003;169
19. Hayashi T., Inoue K., Taniguchi N., Ogasawara M. J. Am. Chem. Soc. 123:2001;9918
20. 7
21. Lautens M., Yoshida M. Org. Lett. 4:2002;123
22. Lautens M., Yoshida M. J. Org. Chem. 68:2003;762
23. Shirakawa E., Takahashi G., Tsuschimoto T., Kawakami Y. Chem. Commun. 2001;2688
24. For the formation of dimeric compound with titane catalyst, see: Launey V., Beaudet I., Quintard J.-P. Synlett. 1997;821
25. Uson R., Oro L.A., Cabeza J. Inorg. Synth. 23:1985;126
26. Hayashi T., Takahashi M., Takaya Y., Ogasawara M. J. Am. Chem. Soc. 124:2002;5052
27. Fujii T., Koike T., Mori A., Osakada K. Synlett. 2002;295
28. Itooka T., Miyaura N. J. Org. Chem. 68:2003;6000. and references cited therein
29. Mori A., Danda Y., Fujii T., Hirabayashi K., Osakada K. J. Am. Chem. Soc. 123:2001;10774
30. No reaction was observed under basic conditions without rhodium catalyst
31. 2 (3.4 mg, 1.5 mol %) and m-TPPTC (12.3 mg, 6 mol %) at room temperature was successively added a water (0.5 mL)/toluene (0.5 mL), phenylboronic acid (152 mg, 1.25 mmol), and oct-4-yne (74 μL, 0.5 mmol). The mixture was heated at 100°C until completion of the reaction and then cooled to room temperature. The alkene was isolated either through separation and extraction with toluene (2 times) or direct filtration on a short pad of silica gel and evaporation under reduced pressure. 90 mg (96%) of 6a were obtained as a pale yellow oil. No further purification was necessary. The purity ( > 95%) was checked by NMR and GC-MS analyses
32. 2O mixture
33. Misumi Y., Masuda T. Macromolecules. 31:1998;7572
34. Yamamoto M., Onitsuka K., Takahashi S. Organometallics. 19:2000;4669
35. For some recent successful reactions based on concentration controls in water or fluorous systems, see: Ryu I., Matsubara H., Yasuda S., Nakamura H., Curran D.P. J. Am. Chem. Soc. 124:2002;12946
36. Xiang J., Orita A., Otera J. Angew. Chem., Int. Ed. 41:2002;4117
37. Kinoshita H., Shinokubo H., Oshima K. J. Am. Chem. Soc. 125:2003;7784
38. Lautens M., Roy A., Fukuoka F., Fagnou K., Martin-Matute B. J. Am. Chem. Soc. 123:2001;5358
39. The m-TPPTC ligand displays a higher basicity than the TPPTS phosphane. This study will be published elsewhere
40. 1H NMR 400 MHz δ=5.48, 5.46 ppm J=1.1 Hz and 7.11, 7.04 ppm J=16.5 Hz)