Palladium-catalyzed heck and suzuki coupling in glycerol
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A. Wolfson
und
C. Dlugy
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/cr950020xSuche in Google Scholar
[2] Crisp, G. T., Chem. Soc. Rev. 27, 427 (1998). http://dx.doi.org/10.1039/a827427z10.1039/a827427zSuche in Google Scholar
[3] Dounay, A. B. and Overman, L. E., Chem. Rev. 103, 2945 (2003). http://dx.doi.org/10.1021/cr020039h10.1021/cr020039hSuche 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.2005.08.054Suche 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-XSuche in Google Scholar
[6] Miyaura, N. and Suzuki, A., Chem. Rev. 95, 2457 (1995). http://dx.doi.org/10.1021/cr00039a00710.1021/cr00039a007Suche 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.200290036Suche 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.200461432Suche in Google Scholar
[9] Reichardt, C., Solvent Effects in Organic Chemistry. Verlag Chemie, Weinheim, 1979. Suche 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. Suche 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)01088-2Suche 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-GSuche 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.2006.03.096Suche 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.2006.04.039Suche 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.2004.10.039Suche 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/ol0266976Suche 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/jo050353mSuche in Google Scholar
[18] Liu, W. J., Xie, Y. X., Yun, L. A., and Li, J. H., Synthesis-Stuttgart 2006, 860. 10.1055/s-2006-926323Suche 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/ol9907771Suche in Google Scholar
[20] Howarth, J. and Dallas, A., Molecules 5, 851 (2000). http://dx.doi.org/10.3390/5060085110.3390/50600851Suche 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;2-8Suche 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/ja00969a025Suche 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.2005.08.019Suche in Google Scholar
[24] Wolfson, A., Dlugy, C., and Shotland, Y., Environ. Chem. Lett., accepted for publication (2006). Suche 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.2006.07.026Suche 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.200400655Suche in Google Scholar
[27] Tierney, J. and Lidström, P., Microwave-Assisted Organic Synthesis. Blackwell, Oxford, 2005. 10.1002/9781444305548Suche 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)00906-1Suche in Google Scholar
[29] Liu, Y. B., Khemtong, C., and Hu, J., Chem. Commun. 2004, 398. 10.1039/B313210MSuche in Google Scholar PubMed
© 2007 Institute of Chemistry, Slovak Academy of Sciences
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Artikel in diesem Heft
- A review of methods for synthesis of nanostructured metals with emphasis on iron compounds
- Effect of selenium oxidation state on cadmium translocation in chamomile plants
- Optimization of ammonium nitrate concentration in single-stage continuous cultures of Aspergillus niger with biomass retention
- Behaviour of inorganic constituents of municipal sewage sludge during fluidized-bed combustion
- Profile distribution of As(III) and As(V) species in soil and groundwater in Bozanta area
- Structure of cyano-bridged Eu(III)—Co(III) bimetallic assembly and its application to photophysical verification of photomagnetic phenomenon
- Synthesis and characterization of oligo-4-[(pyridin-3-ylimino)methyl]phenol
- Relationship between physicochemical properties, lipophilicity parameters, and local anesthetic activity of dibasic esters of phenylcarbamic acid
- Improved DPPH determination for antioxidant activity spectrophotometric assay
- Notes on notation of sodium oxofluoroaluminate anions
- Determination of the enthalpy of fusion of Na3FeF6
- Controlled solvothermal synthesis of PbS quasi-nanorods by calix[4]arene
- Palladium-catalyzed heck and suzuki coupling in glycerol
- Synthesis of new condensed and cyclized coumarin derivatives
- M. Hartman, O. Trnka, and M. Pohořelý: Fluidization behavior of oil-contaminated sand
