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Catalytic Activity of Perhydrobenzimidazolium Salts in Suzuki-Miyaura Coupling Reactions

Year 2014, Volume: 4 Issue: 1, 11 - 17, 27.11.2014

Abstract

1,3-Dialkylperhydrobenzimidazolium chloride salts as N-heterocyclic carbene precursors were synthesised by reaction of secondary amines with ammonium chloride in triethyl orthoformate at 130 ºC. Prepared salts were used as catalyst for coupling reactions of phenylboronic acid with aryl halides and substituted biaryl compounds were obtained in high yields.

References

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  • M. Kertesz, C. H. Choi, S. Yang, Chem. Rev., 2005, 105, 3448.
  • S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron, 2002, 58, 9633.
  • S. Lightowler, M. Hird, Chem. Mater., 2005, 17, 5538.
  • N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun., 1981, 11, 513.
  • M. Gruber, S. Chouzier, K. Koehler, L. Djakovitch, Appl. Catal. A: Gen. 2004, 265, 161. L. Bai, J. Xian, Y. Zhang, Green Chem., 2003, 5, 615.
  • C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, J. Org. Chem., 1999, 64, 3885.
  • F. Chanthavong, N. E. Leadbeater, Tetrahedron Lett., 2006, 47, 1909.
  • R. K. Arvela, N. E. Leadbeater, T. L. Mack, C. M. Kormos, Tetrahedron Lett., 2666, 47, 217.
  • A. F. Littke, G. C. Fu, J. Am. Chem. Soc., 2001, 123, 6989.
  • W. A. Herrmann, V. P. W. Böhm, C. P. Reisinger, J. Organomet. Chem., 1999, 576, 23. K. M. Wu, C. A. Huang, K. F. Peng, and C. T. Chen, Tetrahedron, 2005, 61, 9679.
  • Y. C. Lai, H. Y.Chen, W. C. Hung, C. C. Lin, F. E. Hong, Tetrahedron, 2005, 61, 9484. B. Tao, D. W. Boykin, Tetrahedron Lett., 2003, 44, 7993.
  • P. A. Gossage, H. A. Jenkins, P. N. Yadav, Tetrahedron Lett., 2004, 45, 7689.
  • M. R. Buncmeiser, K. Wurst, J. Am. Chem. Soc., 1999, 121, 11101.
  • S. Iyer, G. M. Kulkarni, C. Ramesh, Tetrahedron, 2004, 60, 2163.
  • T. Mino, Y. Shirae, M. Sakamoto, T. Fujita, J. Org. Chem., 2005, 70, 2191.
  • X. Cui, Y. Zhou, N. Wang, L. Liu, Q. X. Guo, Tetrahedron Lett., 2007, 48, 163.
  • E. Çetinkaya, P.B. Hitchcock, H. A. Jasim, M. F. Lappert, K. J. Spyropoulos, Perkin Trans., 1992, 1, 561.
  • S. Saba, A. Brescia, M. K. Kaloustian, Tetrahedron Lett., 1991, 32, 5031.
  • A. J. Arduengo III, R. Krafczyk, R. Schmutzler, Tetrahedron, 1999, 55, 14523.
  • İ. Özdemir, S. Demir, S. Yaşar, B. Çetinkaya, Appl. Organometal. Chem., 2005, 19, 55. İ. Özdemir, Y. Gök, N. Gürbüz, E. Çetinkaya, B. Çetinkaya, Heteroatom Chem., 2004, 15, 419.
  • İ. Özdemir, Y. Gök, N. Gürbüz, B. Çetinkaya, Turk. J. Chem., 2007, 31, 397.
  • M. Yiğit, Molecules, 2009, 14, 2032.
  • B. Yiğit, M. Yiğit, İ. Özdemir, E. Çetinkaya, Turk. J. Chem., 2010, 34, 327.
  • B. Yiğit, M. Yiğit, İ. Özdemir, E. Çetinkaya, Heterocycles, 2010, 81, 943.
  • M. Yiğit, G. Bayam, B. Yiğit, İ. Özdemir, Heterocycles, 2013, 87, 897.

Perhidrobenzimidazolyum Tuzlarının Suzuki-Miyaura Eşleşme Tepkimelerindeki Katalitik Aktivitesi

Year 2014, Volume: 4 Issue: 1, 11 - 17, 27.11.2014

Abstract

N-Heterosiklik karben öncülleri olan 1,3-dialkilperhidrobenzimidazolyum klorür tuzları, sekonder aminlerin amonyum klorür ile trietil ortoformat içersinde 130 ºC’de ısıtılmaları sonucu sentezlendi. Hazırlanan tuzlar fenilboronik asit ile aril halojenlerin eşleşme reaksiyonlarında katalizör olarak kullanıldı ve yüksek verimlerle sübstitüye biaril bileşikleri elde edildi.

References

  • S. Kaye, J. M. Fox, F. A. Hicks, S. L. Buchwald, Adv. Synth. Catal., 2001, 343, 789.
  • M. Kertesz, C. H. Choi, S. Yang, Chem. Rev., 2005, 105, 3448.
  • S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron, 2002, 58, 9633.
  • S. Lightowler, M. Hird, Chem. Mater., 2005, 17, 5538.
  • N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun., 1981, 11, 513.
  • M. Gruber, S. Chouzier, K. Koehler, L. Djakovitch, Appl. Catal. A: Gen. 2004, 265, 161. L. Bai, J. Xian, Y. Zhang, Green Chem., 2003, 5, 615.
  • C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, J. Org. Chem., 1999, 64, 3885.
  • F. Chanthavong, N. E. Leadbeater, Tetrahedron Lett., 2006, 47, 1909.
  • R. K. Arvela, N. E. Leadbeater, T. L. Mack, C. M. Kormos, Tetrahedron Lett., 2666, 47, 217.
  • A. F. Littke, G. C. Fu, J. Am. Chem. Soc., 2001, 123, 6989.
  • W. A. Herrmann, V. P. W. Böhm, C. P. Reisinger, J. Organomet. Chem., 1999, 576, 23. K. M. Wu, C. A. Huang, K. F. Peng, and C. T. Chen, Tetrahedron, 2005, 61, 9679.
  • Y. C. Lai, H. Y.Chen, W. C. Hung, C. C. Lin, F. E. Hong, Tetrahedron, 2005, 61, 9484. B. Tao, D. W. Boykin, Tetrahedron Lett., 2003, 44, 7993.
  • P. A. Gossage, H. A. Jenkins, P. N. Yadav, Tetrahedron Lett., 2004, 45, 7689.
  • M. R. Buncmeiser, K. Wurst, J. Am. Chem. Soc., 1999, 121, 11101.
  • S. Iyer, G. M. Kulkarni, C. Ramesh, Tetrahedron, 2004, 60, 2163.
  • T. Mino, Y. Shirae, M. Sakamoto, T. Fujita, J. Org. Chem., 2005, 70, 2191.
  • X. Cui, Y. Zhou, N. Wang, L. Liu, Q. X. Guo, Tetrahedron Lett., 2007, 48, 163.
  • E. Çetinkaya, P.B. Hitchcock, H. A. Jasim, M. F. Lappert, K. J. Spyropoulos, Perkin Trans., 1992, 1, 561.
  • S. Saba, A. Brescia, M. K. Kaloustian, Tetrahedron Lett., 1991, 32, 5031.
  • A. J. Arduengo III, R. Krafczyk, R. Schmutzler, Tetrahedron, 1999, 55, 14523.
  • İ. Özdemir, S. Demir, S. Yaşar, B. Çetinkaya, Appl. Organometal. Chem., 2005, 19, 55. İ. Özdemir, Y. Gök, N. Gürbüz, E. Çetinkaya, B. Çetinkaya, Heteroatom Chem., 2004, 15, 419.
  • İ. Özdemir, Y. Gök, N. Gürbüz, B. Çetinkaya, Turk. J. Chem., 2007, 31, 397.
  • M. Yiğit, Molecules, 2009, 14, 2032.
  • B. Yiğit, M. Yiğit, İ. Özdemir, E. Çetinkaya, Turk. J. Chem., 2010, 34, 327.
  • B. Yiğit, M. Yiğit, İ. Özdemir, E. Çetinkaya, Heterocycles, 2010, 81, 943.
  • M. Yiğit, G. Bayam, B. Yiğit, İ. Özdemir, Heterocycles, 2013, 87, 897.
There are 26 citations in total.

Details

Primary Language Turkish
Journal Section Research Articles
Authors

Murat Yiğit This is me

Publication Date November 27, 2014
Published in Issue Year 2014 Volume: 4 Issue: 1

Cite

APA Yiğit, M. (2014). Perhidrobenzimidazolyum Tuzlarının Suzuki-Miyaura Eşleşme Tepkimelerindeki Katalitik Aktivitesi. Adıyaman University Journal of Educational Sciences, 4(1), 11-17.

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