Heck reactions in supercritical carbon dioxide using organometallic complex catalysts

High Pressure Research

Volumn 20, Issue 1-6, 2001, Pages 131-142

  Bhanage, B M ^a,c   Ikushima, Y ^b,c   Shirai, M ^a   Arai, M ^a,c  

^a TOHOKU UNIVERSITY   (Japan)

^b TOHOKU NATL INDUST RES INSTITUTE   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Aryl halide; Biphasic catalysis; Carbon dioxide; Heck reaction; Palladium; Solvent; Solvent effects

Indexed keywords

EID: 0001306727     PISSN: 08957959     EISSN: None     Source Type: Journal    
DOI: 10.1080/08957950108206160     Document Type: Article

References (27)

1. See papers, In: Chem. Rev., 99 (1999).
2. Jessop, P. G., Ikaria, T. and Noyori, R. (1995). Homogeneous catalysis in supercritical fluids, Science, 269, 1065.
3. Saito, S. (1995). Research activities on supercritical fluid science and technology in Japan - A review, J. Supercrit. Fluids, 8, 177.
4. Kaupp, G. (1994). Reactions in supercritical carbon dioxide, Angew Chem. Int. Ed. Engl., 33, 1452.
5. Johnston, K. P. and Penninger, J. M. L. Eds., Supercritical Fluid Science and Technology, ACS Symp. Ser. 406, Am. Chem. Soc., Washington DC, 1989.
6. Poliakoff, M., Howdle, S. M. and Kazarian, S. G. (1995). Vibrational spectroscopy in supercritical fluids: from analysis and hydrogen bonding to polymers and synthesis, Angew Chem. Int. Ed. Engl., 34, 1275.
7. Jessop, P. G., Ikariya, T. and Noyori, R. (1994). Homogeneous catalytic hydrogenation of supercritical carbon dioxide, Nature, 368, 231.
8. Jessop, P. G., Hsiao, Y., Ikariya, T. and Noyori, R. (1996). Homogeneous catalysis in supercritical fluids: hydrogenation of supercritical carbon dioxide to formic acid, alkyl formates, and formamides, J. Am. Chem. Soc., 118, 344.
9. Furstner, A., Koch, D., Langemann, K., Leitner, W. and Six, C. (1997). Olefin metathesis in compressed carbon dioxide, Angew Chem. Int. Ed. Engl., 36, 2466.
10. Rathke, J. W., Klingler, R. J. and Krause, T. R. (1991). Propylene hydroformylation in supercritical carbon dioxide, Organometallics, 10, 1350.
11. Kainz, S. and Leitner, W. (1998). Catalytic asymmetric hydroformylation in the presence of compressed carbon dioxide, Catal. Lett., 55, 223.
12. Cornils, B. and Herrmann, W. A. Eds., Applied Homogeneous Catalysis by Organometallic Complexes, Wiley-VCH, Weinheim, 1996.
13. Cornils, B., Herrmann, W. A. and Eckl, R. W. (1997). Industrial aspects of aqueous catalysis, J. Mol. Catal. A: Chem., 116, 27.
14. Herrmann, W. A. and Cornils, B. (1997). Organometallic homogeneous catalysis -Quo vadis? Angew. Chem. Int. Ed. Engl., 36, 1048.
15. Arhancet, J. P., Davis, M. E., Merola, J. S. and Hanson, B. E. (1989). Hydroformylation by supported aqueous-phase catalysis: a new class of heterogeneous catalysts, Nature, 339, 454.
16. Chaudhari, R. V., Bhanage, B. M., Deshpande, R. M. and Delmas, H. (1995). Enhancement of interfacial catalysis in a biphasic system using catalyst-binding ligands, Nature, 373, 501.
17. Jenck, J. and Morel, D. (1987). Preparation of tri-(m-sulfophenyl)-phosphine, US Patent, No. 4668824.
18. Tonks, L., Anson, M. S., Hellgardt, K., Mirza, A. R., Thompson, D. F. and Williams, J. M. J. (1997). Palladium catalyzed Heck reactions and allylic substitution reactions using glass bead technology, Tetrahedron Lett., 38, 4319.
19. Carroll, M. A. and Holmes, A. B. (1998). Palladium-catalyzed carbon-carbon bond formation in supercritical carbon dioxide, Chem. Commun., pp. 1395.
20. Morita, D. K., Pesiri, D. R., David, S. A., Glaze, W. H. and Tumas, W. (1998). Palladium-catalyzed cross-coupling reactions in supercritical carbon dioxide, Chem. Commun., pp. 1397.
21. Shezad, N., Oakes, R. S., Clifford, A. A. and Rayner, C. M. (1999). Use of fluorinated palladium sources for efficient Pd-catalyzed coupling reactions in supercritical carbon dioxide, Tetrahedron Lett., 40, 2221.
22. Cacchi, S., Fabrizi, G., Gasparrini, F. and Villani, C. (1999). Carbon-carbon bond forming reactions in supercritical carbon dioxide in the presence of a supported palladium catalyst, Synlett, pp. 345.
23. Dobbs, J. M., Wong, J. M., Lahiere, R. J. and Johnston, K. P. (1987). Modification of supercritical fluid phase behavior using polar cosolvents, Ind. Eng. Chem. Res., 26, 56.
24. (a) Kaminishi, G., Takano, S., Yokoyama, C. and Takahashi, S. (1989). Concentration of triethylene glycol, diethylene glycol and ethylene glycol in supercritical carbon dioxide up to 16MPa at 313.15 and 333.15 K, Fluid Phase Equil., 52, 365;
25. (b) King, M. B., Mubarak, A., Kim, J. D. and Bott, T. R. (1992). The mutual solubilities of water with supercritical and liquid carbon dioxide, J. Supercrit. Fluids, 5, 296;
26. (c) Macnaughton, S. J. and Foster, N. R. (1994). Solubility of DDT and 2,4-D in supercritical carbon dioxide and supercritical carbon dioxide saturated with water, Ind. Eng. Chem. Res., 33, 2757.
27. Bhanage, B. M., Zhao, F.-Y., Shirai, M. and Arai, M. (1998). Comparison of activity and selectivity of various metal-TPPTS complex catalysts in ethylene glycol - toluene biphasic Heck vinylation reactions od iodobenzene, Tetrahedron Lett., 39, 9509.