SavedAdd your journal

Journals / Turkish Journal of Chemistry / 2015 / Cilt: 39 - Sayı: 6

Resorcinarene-mono-benzimidazolium salts as NHC ligands for Suzuki--Miyaura cross-couplings catalysts

ÜMİT İŞCİ
MUHİTTİN AYGÜN
RESUL SEVİNCEK
YUNUS ZORLU
FABIENNE DUMOULIN
Pages
1300–1309
Publication Date
2015-12-04
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

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

The highest conversion was achieved for arylation of 4-bromotoluene using the resorcinarenyl mono-dimethylbenzimidazolium salt.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Two mono-benzimidazolium salts of resorcinarene have been prepared and used as ligands in Suzuki--Miyaura cross-coupling reactions.
📊
Key Findings & Data:They have been fully characterized by $^{1}$H and $^{13}$C NMR, MALDI, and FT-IR spectroscopic methods, and their structures were confirmed by X-ray diffraction analysis.
💡
Conclusion & Impact:The highest conversion was achieved for arylation of 4-bromotoluene using the resorcinarenyl mono-dimethylbenzimidazolium salt.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Suzuki--Miyaura reaction · resorcinarene · cavitand

Abstract

Two mono-benzimidazolium salts of resorcinarene have been prepared and used as ligands in Suzuki--Miyaura cross-coupling reactions. They have been fully characterized by $^{1}$H and $^{13}$C NMR, MALDI, and FT-IR spectroscopic methods, and their structures were confirmed by X-ray diffraction analysis. These two new resorcinarene-based mono-benzimidazolium salts showed good catalytic activity for coupling reactions in DMF. The highest conversion was achieved for arylation of 4-bromotoluene using the resorcinarenyl mono-dimethylbenzimidazolium salt.

Özet

Two mono-benzimidazolium salts of resorcinarene have been prepared and used as ligands in Suzuki--Miyaura cross-coupling reactions. They have been fully characterized by $^{1}$H and $^{13}$C NMR, MALDI, and FT-IR spectroscopic methods, and their structures were confirmed by X-ray diffraction analysis. These two new resorcinarene-based mono-benzimidazolium salts showed good catalytic activity for coupling reactions in DMF. The highest conversion was achieved for arylation of 4-bromotoluene using the resorcinarenyl mono-dimethylbenzimidazolium salt.

🔖

Cite This Article

İŞCİ, Ü., AYGÜN, M., SEVİNCEK, R., ZORLU, Y., DUMOULIN, F. (2015). Resorcinarene-mono-benzimidazolium salts as NHC ligands for Suzuki--Miyaura cross-couplings catalysts. Turkish Journal of Chemistry, Cilt: 39 - Sayı: 6, 1300–1309. https://ajindex.com/articles/184609

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (17)

  1. Grushin, V. V.; Alper, H. In: Topics in Organometallic Chemistry, Vol. 3; Murai, S., Ed. Springer: New York, NY, USA, 1999, pp. 193–226.
  2. Beller, M.; Riermeier, T. H. In: Transition Metals for Organic Synthesis, Vol. 1; Beller, M.; Bolm, C., Eds. Wiley- VCH: Weinheim, Germany, 1998, pp. 184–193.
  3. Suzuki, A. J. Organomet. Chem. 1999, 576, 147–168.
  4. Kim, Y. H.; Webster, W. W. J. Am. Chem. Soc. 1990, 112, 4592–4593.
  5. Martin, R.; Buchwald, S. L. Acc. Chem. Res., 2008, 41, 1461–1473. Ozdemir, ˙I.; C¸ etinkaya, B.; Demir, S.; G¨urb¨uz, N. Catal. Lett. 2004, 97, 37–40. ¨ ¨ Ozdemir, ˙I.; C¸ etinkaya, B.; Demir, S. J. Mol. Cat. A 2004, 208, 109–114. T¨urkmen, H.; Can, R.; C¸ etinkaya, B. Dalton Trans. 2009, 7039–7044.
  6. Huang, W.; Guo, E. P.; Xiao, Y. J.; Zhu, M. F.; Zou, G.; Tang, J. Tetrahedron 2005, 61, 9783–9790. ¨ Ozdemir, ˙I.; G¨ok, Y.; G¨urb¨uz, N.; C¸ etinkaya, E.; C¸ etinkaya, B. Synth. Commun. 2004, 34, 4135–4144.
  7. Zakharova, L. Y.; Valeeva, F. G.; Ibragimova, A. R.; Voronin, M. A.; Kudryavtseva, L. A.; Syakaev, V. V.; Kazakova, E. K.; Morozova, Y. E.; Makarova, N. A.; Mel’nikova, N. B. et al. Russ. Chem. Bull. Int. Ed. 2008, 57, –382. Zakharova, L. Y.; Syakaev, V. V.; Voronin, M. A.; Valeeva, F. G.; Ibragimova, A. R.; Ablakova, Y. R.; Kazakova, E. K.; Latypov, S. K.; Konovalov, A. I. J. Phys. Chem. C 2009, 113, 6182–6190.
  8. Pashirova, T. N.; Lukashenko, S. S.; Kosacheva, E. M.; Rizvanova, L. Z.; Gainanova, G. A.; Knyazeva, I. R.; Burilov, A. R.; Kudryavtseva, L. A.; Konovalov, A. I. Russ. Chem. Bull. Int. Ed. 2007, 56, 959–966.
  9. Pashirova, T. N.; Lukashenko, S. S.; Kosacheva, E. M.; Leonova, M. V.; Vaganova, L. I.; Burilov, A. R.; Pudovik, M. A.; Kudryavtseva, L. A.; Konovalov, A. I. Russ. J. Gen. Chem. 2008, 78, 402–409.
  10. Shirakawa, S.; Shimizu, S. Synlett 2008, 10, 1539–1542.
  11. Arnott, G.; Hunter, R.; Su, H. Tetrahedron 2006, 62, 977–991.
  12. Arnott, G.; Hunter, R. Tetrahedron 2006, 62, 992–1000. S¸ahin, N.; S´emeril, D.; Brenner, E.; Matt, D.; ¨Ozdemir, I.; Kaya, C.; Toupet, L. Chem. Cat. Chem. 2013, 5, –1125. El Moll, H.; S´emeril, D.; Matt, D.; Youinou, M. T.; Toupet, L. Org. Biomol. Chem. 2009, 7, 495–501.
  13. El Moll, H.; S´emeril, D.; Matt, D.; Toupet, L. Eur. J. Org. Chem. 2010, 1158–1168.
  14. El Moll, H.; S´emeril, D.; Matt, D.; Toupet, L. Adv. Synth. Catal. 2010, 352, 901–908.
  15. El Moll, H.; S´emeril, D.; Matt, D.; Toupet, L.; Harrowfield, J. J. Org. Biomol. Chem. 2012, 10, 372–382.
  16. Frank, M.; Maas, G.; Schatz, J. Eur. J. Org. Chem. 2004, 607–613.
  17. Frank, M.; Maas, G.;