Journals / Turkish Journal of Chemistry / 2015 / Cilt: 39 - Sayı: 2

The synthesis of 1,3-dialkyl-4-methylimidazolinium salts and their application in palladium catalyzed Heck coupling reactions

Pages
281
Publication Date
2015-08-13
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

The corresponding Heck products were obtained in good yields.

📌 3 Key Takeaways

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Objective & Hypothesis:Seven novel 1,3-dialkyl-4-methylimidazolinium chloride salts 3a--g were prepared as precursors of N-heterocyclic carbenes by reacting N,N'-alkyl-1,2-diaminopropane, triethyl orthoformate, and ammonium chloride.
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Key Findings & Data:The salts were characterized spectroscopically.
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Conclusion & Impact:The corresponding Heck products were obtained in good yields.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Heck reaction · imidazolinium salt · palladium

Abstract

Seven novel 1,3-dialkyl-4-methylimidazolinium chloride salts 3a--g were prepared as precursors of N-heterocyclic carbenes by reacting N,N'-alkyl-1,2-diaminopropane, triethyl orthoformate, and ammonium chloride. The salts were characterized spectroscopically. The in situ prepared palladium complexes derived from the imidazolinium salts and palladium acetate were used as catalyst in Heck coupling reactions between aryl bromides and styrene. The corresponding Heck products were obtained in good yields.

Özet

Seven novel 1,3-dialkyl-4-methylimidazolinium chloride salts 3a--g were prepared as precursors of N-heterocyclic carbenes by reacting N,N'-alkyl-1,2-diaminopropane, triethyl orthoformate, and ammonium chloride. The salts were characterized spectroscopically. The in situ prepared palladium complexes derived from the imidazolinium salts and palladium acetate were used as catalyst in Heck coupling reactions between aryl bromides and styrene. The corresponding Heck products were obtained in good yields.

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Cite This Article

YİĞİT, M., BAYAM, G., YİĞİT, B., ÖZDEMİR, İ. (2015). The synthesis of 1,3-dialkyl-4-methylimidazolinium salts and their application in palladium catalyzed Heck coupling reactions. Turkish Journal of Chemistry, Cilt: 39 - Sayı: 2, 281. https://ajindex.com/articles/185141

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References (28)

  1. Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320–2322.
  2. Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581. Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press:
  3. London, UK, 1985.
  4. Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945–2963.
  5. Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10–11.
  6. Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989–7000.
  7. Feuerstein, M.; Doucet, H.; Santelli, M. J. Org. Chem. 2001, 66, 5923–5925.
  8. Moore, L. R.; Shaughnessy, K. H. Org. Lett. 2004, 6, 225–228.
  9. Ehrentraut, A.; Zapf, A.; Beller, M. Synlett 2000, 1589–1592.
  10. Lee, D. H.; Taher, A.; Hossain, S.; Jin, M. J. Org. Lett. 2011, 13, 5540–5543.
  11. Sabounchei, S. J.; Ahmedi, M.; Panahimehr, M.; Bagherjeri, F. A.; Nasri, Z. J. Mol. Catal. A: Chem. 2014, 383–384, 249–259.
  12. Herrmann, W. A.; Reisinger, C. P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93–98.
  13. Han, Y.; Huynh, H. W.; Koh, L. L. J. Organomet. Chem. 2007, 692, 3606–3613. Ozdemir, ˙I.; Yi˘git, M.; C¸ etinkaya, E., C¸ etinkaya, B. Appl. Organometal. Chem. 2006, 20, 187–192. ¨ Yang, W. H.; Lee, C. S.; Pal, S.; Chen, Y. N.; Hwang, W. S.; Lin, I. J. B.; Wang, J. C. J. Organomet. Chem. 2008, 693, 3729–3740.
  14. Lee, C. S.; Lai, Y. B.; Lin, W. J.; Zhuang, R. R.; Hwang, W. S. J. Organomet. Chem. 2013, 724, 235–243.
  15. Rao, G. K.; Kumar, A.; Singh, M. P.; Kumar, A.; Biradar, A. M.; Singh, A. K. J. Organomet. Chem. 2014, 753, 42– Wu, K. M.; Huang, C. A.; Peng, K. F.; Chen, C. T. Tetrahedron 2005, 61, 9679–9687.
  16. Lai, Y. C.; Chen, H. Y.; Hung, W. C.; Lin, C. C.; Hong, F. E. Tetrahedron 2005, 61, 9484–9489.
  17. Tao, B.; Boykin, D. W. Tetrahedron Lett. 2003, 44, 7993–7996.
  18. Gossage, P. A.; Jenkins, H. A.; Yadav, P. N. Tetrahedron Lett. 2004, 45, 7689–7691.
  19. Buncmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101–11107.
  20. Iyer, S.; Kulkarni, G. M.; Ramesh, C. Tetrahedron 2004, 60, 2163–2172.
  21. Mino, T.; Shirae, Y.; Sakamoto, M.; Fujita, T. J. Org. Chem. 2005, 70, 2191–2194.
  22. Cui, X.; Zhou, Y.; Wang, N., Liu, L.; Guo, Q. X. Tetrahedron Lett. 2007, 48, 163–167.
  23. Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2000, 46, 181–222.
  24. Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290–1309.
  25. Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2239–2246.
  26. Viciu, M, S.; Kelly, R. A.; Stevens, E. D.; Naud, F.; Studer, M.; Nolan, S. P. Org. Lett. 2003, 5, 1479–1482.
  27. Matsubara, K.; Ueno, K.; Koga, Y.; Hara, K. J. Org. Chem. 2007, 72, 5069–5076.
  28. Trindade, A. F.; Gois, P. M. P.; Veiros, L. F.; Andre, V.; Dua