Startseite Effect of microwave irradiation on the reactivity of chloroarenes in Suzuki—Miyaura reaction
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Effect of microwave irradiation on the reactivity of chloroarenes in Suzuki—Miyaura reaction

  • V. Poláčková EMAIL logo und Š. Toma
Veröffentlicht/Copyright: 1. Februar 2007
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Abstract

Simple catalytic systems for the Suzuki—Miyaura reaction of aryl chlorides under microwave conditions were tested. Microwave irradiation facilitated the reaction course. The catalyst, base, and solvent effect were studied and two reaction systems offered reasonable to high yields within a short time.

[1] Miyaura, N. A. and Suzuki, A., Chem. Rev. 95, 2457 (1995). http://dx.doi.org/10.1021/cr00039a00710.1021/cr00039a007Suche in Google Scholar

[2] Suzuki, A., Chem. Commun. 2005, 4759. 10.1039/b507375hSuche in Google Scholar

[3] Kotha, S., Lahiri, K., and Kashinath, D., Tetrahedron 58, 9633 (2002). http://dx.doi.org/10.1016/S0040-4020(02)01188-210.1016/S0040-4020(02)01188-2Suche in Google Scholar

[4] Tao, X., Zhao, Y., and Shen, D., Synlett 2004, 359. Suche in Google Scholar

[5] Rosa, G. R., Ebeling, G., Dupont, J., and Monteiro, A., Synthesis-Stuttgart 2003, 2894. Suche in Google Scholar

[6] Littke, A. F. and Fu, G. C., Angew. Chem., Int. Ed. Engl. 41, 4177 (2002). http://dx.doi.org/10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-USuche in Google Scholar

[7] Leadbeater, N. E. Chem. Commun. 2005, 2881. 10.1039/b500952aSuche in Google Scholar

[8] Leadbeater, N. E. and Marco, M., J. Org. Chem. 68, 5660 (2003). http://dx.doi.org/10.1021/jo034230i10.1021/jo034230iSuche in Google Scholar

[9] Arvela, R. K., Leadbeater, N. E., Sangi, M. S., Williams, V. A., Granados, P., and Singer, R. D., J. Org. Chem. 70, 161 (2005). http://dx.doi.org/10.1021/jo048531j10.1021/jo048531jSuche in Google Scholar

[10] Alimardov, A., de Vondervoort, L. S. V., de Vries, A. H. M., and de Vries, J. G., Adv. Synth. Catal. 346, 1812 (2004). http://dx.doi.org/10.1002/adsc.20040421010.1002/adsc.200404210Suche in Google Scholar

[11] Liu, L., Zhang, Y., and Wang, Y., J. Org. Chem. 70, 6122 (2005). http://dx.doi.org/10.1021/jo050724z10.1021/jo050724zSuche in Google Scholar

[12] 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

[13] Zhang, G. L., Synthesis-Stuttgart 2005, 537. 10.1055/s-2004-837298Suche in Google Scholar

[14] Gordon, R. S. and Holmes, A. B., Chem. Commun. 2002, 640. 10.1039/b111430aSuche in Google Scholar

[15] Mathews, C. J., Smith, P. J., and Welton, T., Chem. Commun. 2000, 1249. 10.1039/b002755nSuche in Google Scholar

[16] Kabalka, G. W., Pagni, R. M., and Hair, C. M., Org. Lett. 1, 1423 (2000). http://dx.doi.org/10.1021/ol990972f10.1021/ol990972fSuche in Google Scholar

[17] Littke, A. F. and Fu, G. C., Angew. Chem., Int. Ed. Engl. 37, 3387 (1998). http://dx.doi.org/10.1002/(SICI)1521-3773(19981231)37:24<3387::AID-ANIE3387>3.0.CO;2-P10.1002/(SICI)1521-3773(19981231)37:24<3387::AID-ANIE3387>3.0.CO;2-PSuche in Google Scholar

[18] Nájera, C., Gil-Molto, J., and Karlström, S., Adv. Synth. Catal. 346, 1798 (2004). http://dx.doi.org/10.1002/adsc.20040419510.1002/adsc.200404195Suche in Google Scholar

[19] Leadbeater, N. E. and Marco, M., Org. Lett. 4, 2973 (2002). http://dx.doi.org/10.1021/ol026390710.1021/ol0263907Suche in Google Scholar

[20] Navarro, O., Kaur, H., Mahjoor, P., and Nolan, S. P., J. Org. Chem. 69, 3173 (2004). http://dx.doi.org/10.1021/jo035834p10.1021/jo035834pSuche in Google Scholar

[21] Bedford, R. B., Butts, C. P., Hurst, T. E., and Lindström, P., Adv. Synth. Catal. 346, 1627 (2004). http://dx.doi.org/10.1002/adsc.20040414410.1002/adsc.200404144Suche in Google Scholar

[22] Arvela, R. K. and Leadbeater, N. E., Org. Lett. 7, 2101 (2005). http://dx.doi.org/10.1021/ol050338410.1021/ol0503384Suche in Google Scholar

[23] Kabalka, G. W., Wang, L., Pagni, R. M., Hair, M., and Namboodiri, V., Synthesis-Stuttgart 2003, 217. Suche in Google Scholar

[24] Poláčková, V., Hut’ka, M., and Toma, Š., Ultrason. Sonochem. 12, 99 (2005). http://dx.doi.org/10.1016/j.ultsonch.2004.05.01110.1016/j.ultsonch.2004.05.011Suche in Google Scholar

[25] Cravotto, G., Beggiato, M., Penoni, A., Palmisano, G., Tollari, S., Leveque, J. M., and Bonrath, W., Tetrahedron Lett. 46, 2267 (2005). http://dx.doi.org/10.1016/j.tetlet.2005.02.01510.1016/j.tetlet.2005.02.015Suche in Google Scholar

[26] Inada, K. and Miyaura, N., Tetrahedron 56, 8657 (2000). http://dx.doi.org/10.1016/S0040-4020(00)00814-010.1016/S0040-4020(00)00814-0Suche in Google Scholar

[27] LeBlond, C. R., Andrews, A. T., Sun, Y., and Sowa, J. R., Org. Lett. 3, 1555 (2001). http://dx.doi.org/10.1021/ol015850d10.1021/ol015850dSuche in Google Scholar

[28] Spivey, A. C., Diaper, C. M., Adams, H., and Rudge, A. J., J. Org. Chem. 65, 5253 (2000). http://dx.doi.org/10.1021/jo000401x10.1021/jo000401xSuche in Google Scholar PubMed

[29] Echavarren, A. M. and Stille, J. K., J. Am. Chem. Soc. 109, 5478 (1987). http://dx.doi.org/10.1021/ja00252a02910.1021/ja00252a029Suche in Google Scholar

[30] Farina, V., Krishnan, B., Marshall, D. R., and Roth, G. P., J. Org. Chem. 58, 5434 (1993). http://dx.doi.org/10.1021/jo00072a02810.1021/jo00072a028Suche in Google Scholar

[31] Wallow, T. I. and Novak, B. M., J. Org. Chem. 59, 5034 (1994). http://dx.doi.org/10.1021/jo00096a05610.1021/jo00096a056Suche in Google Scholar

[32] Mowery, M. E. and DeShong, P. H., J. Org. Chem. 64, 1684 (1999). http://dx.doi.org/10.1021/jo982463h10.1021/jo982463hSuche in Google Scholar PubMed

[33] Cahiez, G., Lepifre, F., and Ramiandrasoa, P., Synthesis 1999, 2138. 10.1055/s-1999-3644Suche in Google Scholar

[34] Moore, L. R. and Shaughnessy, K. H., Org. Lett. 6, 225 (2004). http://dx.doi.org/10.1021/ol036028810.1021/ol0360288Suche in Google Scholar PubMed

Published Online: 2007-2-1
Published in Print: 2007-2-1

© 2007 Institute of Chemistry, Slovak Academy of Sciences

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