Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter June 1, 2007

Palladium-catalyzed heck and suzuki coupling in glycerol

  • A. Wolfson EMAIL logo and C. Dlugy
From the journal Chemical Papers

Abstract

The Heck coupling of halobenzenes with various alkenes and the Suzuki cross coupling of halobenzenes with phenylboronic acid were successfully performed in glycerol as the reaction solvent using homogeneous and heterogeneous palladium catalysts. Glycerol is a renewable and recyclable green solvent that is able to dissolve organic substrates, inorganic bases, and palladium complexes, and that allows easy isolation of the reaction product by simple extraction with glycerol-immiscible solvents such as diethyl ether, hexane, and dichloromethane.

[1] Negishi, E. I., Coperet, C., Ma, S. M., Liou, S. Y., and Liu, F., Chem. Rev. 96, 365 (1996). http://dx.doi.org/10.1021/cr950020x10.1021/cr950020xSearch in Google Scholar

[2] Crisp, G. T., Chem. Soc. Rev. 27, 427 (1998). http://dx.doi.org/10.1039/a827427z10.1039/a827427zSearch in Google Scholar

[3] Dounay, A. B. and Overman, L. E., Chem. Rev. 103, 2945 (2003). http://dx.doi.org/10.1021/cr020039h10.1021/cr020039hSearch in Google Scholar

[4] Alonso, F., Beletskaya, I. P., and Yus, M., Tetrahedron 61, 11771 (2005). http://dx.doi.org/10.1016/j.tet.2005.08.05410.1016/j.tet.2005.08.054Search in Google Scholar

[5] Suzuki, A., J. Organomet. Chem. 653, 83 (2002). http://dx.doi.org/10.1016/S0022-328X(02)01269-X10.1016/S0022-328X(02)01269-XSearch in Google Scholar

[6] Miyaura, N. and Suzuki, A., Chem. Rev. 95, 2457 (1995). http://dx.doi.org/10.1021/cr00039a00710.1021/cr00039a007Search in Google Scholar

[7] Stambuli, J. P., Kuwano, R., and Hartwig, J. F., Angew. Chem., Int. Ed. Engl. 41, 4746 (2002). http://dx.doi.org/10.1002/anie.20029003610.1002/anie.200290036Search in Google Scholar

[8] Frisch, A. C. and Beller, M., Angew. Chem., Int. Ed. Engl. 44, 674 (2005). http://dx.doi.org/10.1002/anie.20046143210.1002/anie.200461432Search in Google Scholar

[9] Reichardt, C., Solvent Effects in Organic Chemistry. Verlag Chemie, Weinheim, 1979. Search in Google Scholar

[10] Herrmann, W. A. and Reisinger, C.-P., in Aqueous-Phase Organometallic Catalysis (Cornils, B. and Herrmann, W. A., Editors). Wiley-VCH, Weinheim, 1998. Search in Google Scholar

[11] Genêt, J. P. and Savignac, M., J. Organomet. Chem. 576, 305 (1999). http://dx.doi.org/10.1016/S0022-328X(98)01088-210.1016/S0022-328X(98)01088-2Search in Google Scholar

[12] Manabe, K. and Kobayashi, S., Chem. Eur. J. 8, 4095 (2002). http://dx.doi.org/10.1002/1521-3765(20020916)8:18<4094::AID-CHEM4094>3.0.CO;2-G10.1002/1521-3765(20020916)8:18<4094::AID-CHEM4094>3.0.CO;2-GSearch in Google Scholar

[13] Yan, J., Jin, H. W., and Shan, S., Tetrahedron 62, 5603 (2006). http://dx.doi.org/10.1016/j.tet.2006.03.09610.1016/j.tet.2006.03.096Search in Google Scholar

[14] Korolev, D. N. and Bumagin, N. A., Tetrahedron Lett. 47, 4225 (2006). http://dx.doi.org/10.1016/j.tetlet.2006.04.03910.1016/j.tetlet.2006.04.039Search in Google Scholar

[15] Luo, C. C., Zhang, Y. H., and Wang, Y. G., J. Mol. Catal. A 229, 7 (2005). http://dx.doi.org/10.1016/j.molcata.2004.10.03910.1016/j.molcata.2004.10.039Search in Google Scholar

[16] Chandrasekhar, S., Narsihmulu, C., Sultana, S. S., and Reddy, N. R., Org. Lett. 4, 4399 (2002). http://dx.doi.org/10.1021/ol026697610.1021/ol0266976Search in Google Scholar

[17] Li, J. H., Liu, W. J., and Xie, Y. X., J. Org. Chem. 70, 5409 (2005). http://dx.doi.org/10.1021/jo050353m10.1021/jo050353mSearch in Google Scholar

[18] Liu, W. J., Xie, Y. X., Yun, L. A., and Li, J. H., Synthesis-Stuttgart 2006, 860. 10.1055/s-2006-926323Search in Google Scholar

[19] Carmichael, A. J., Earle, M. J., Holbrey, J. D., McCormac, P. B., and Seddon, K. R., Org. Lett. 1, 997 (1999). http://dx.doi.org/10.1021/ol990777110.1021/ol9907771Search in Google Scholar

[20] Howarth, J. and Dallas, A., Molecules 5, 851 (2000). http://dx.doi.org/10.3390/5060085110.3390/50600851Search in Google Scholar

[21] Böhm, V. P. W. and Herrmann, W. A., Chem. Eur. J. 6, 1017 (2000). http://dx.doi.org/10.1002/(SICI)1521-3765(20000317)6:6<1017::AID-CHEM1017>3.0.CO;2-810.1002/(SICI)1521-3765(20000317)6:6<1017::AID-CHEM1017>3.0.CO;2-8Search in Google Scholar

[22] Szmant, H. H. and Roman, M. N., J. Am. Chem. Soc. 88, 4034 (1966). http://dx.doi.org/10.1021/ja00969a02510.1021/ja00969a025Search in Google Scholar

[23] Wong, H. T., Han, S. J., and Livingston, A. G., Chem. Eng. Sci. 61, 1338 (2006). http://dx.doi.org/10.1016/j.ces.2005.08.01910.1016/j.ces.2005.08.019Search in Google Scholar

[24] Wolfson, A., Dlugy, C., and Shotland, Y., Environ. Chem. Lett., accepted for publication (2006). Search in Google Scholar

[25] Wolfson, A., Dlugy, C., Tavor, D., Blumenfeld, J., and Shotland, Y., Tetrahedron: Asymmetry 17, 2043 (2006). http://dx.doi.org/10.1016/j.tetasy.2006.07.02610.1016/j.tetasy.2006.07.026Search in Google Scholar

[26] Kappe, C. O., Angew. Chem., Int. Ed. Engl. 43, 6250 (2004). http://dx.doi.org/10.1002/anie.20040065510.1002/anie.200400655Search in Google Scholar

[27] Tierney, J. and Lidström, P., Microwave-Assisted Organic Synthesis. Blackwell, Oxford, 2005. 10.1002/9781444305548Search in Google Scholar

[28] Lidström, P., Tierney, J., Wathey, B., and Westman, J., Tetrahedron 57, 9225 (2001). http://dx.doi.org/10.1016/S0040-4020(01)00906-110.1016/S0040-4020(01)00906-1Search in Google Scholar

[29] Liu, Y. B., Khemtong, C., and Hu, J., Chem. Commun. 2004, 398. 10.1039/B313210MSearch in Google Scholar PubMed

Published Online: 2007-6-1
Published in Print: 2007-6-1

© 2007 Institute of Chemistry, Slovak Academy of Sciences

Downloaded on 5.5.2024 from https://www.degruyter.com/document/doi/10.2478/s11696-007-0026-3/html
Scroll to top button