ÜMİT İŞCİ, MUHİTTİN AYGÜN, RESUL SEVİNCEK, YUNUS ZORLU, FABIENNE DUMOULIN

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

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.

Anahtar Kelimeler:

Suzuki--Miyaura reaction, resorcinarene, cavitand, N-heterocyclic carbene, benzimidazolium salt, catalyst

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

Keywords:

Suzuki--Miyaura reaction, resorcinarene, cavitand, N-heterocyclic carbene, benzimidazolium salt, catalyst,

PDF

___

Grushin, V. V.; Alper, H. In: Topics in Organometallic Chemistry, Vol. 3 ; Murai, S., Ed. Springer: New York, NY, USA, 1999, pp. 193–226.
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.
Suzuki, A. J. Organomet. Chem. 1999, 576, 147–168.
Kim, Y. H.; Webster, W. W. J. Am. Chem. Soc. 1990, 112, 4592–4593.
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.
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.
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.
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.
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.
Shirakawa, S.; Shimizu, S. Synlett 2008, 10, 1539–1542.
Arnott, G.; Hunter, R.; Su, H. Tetrahedron 2006, 62, 977–991.
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.
El Moll, H.; S´emeril, D.; Matt, D.; Toupet, L. Eur. J. Org. Chem. 2010, 1158–1168.
El Moll, H.; S´emeril, D.; Matt, D.; Toupet, L. Adv. Synth. Catal. 2010, 352, 901–908.
El Moll, H.; S´emeril, D.; Matt, D.; Toupet, L.; Harrowfield, J. J. Org. Biomol. Chem. 2012, 10, 372–382.
Frank, M.; Maas, G.; Schatz, J. Eur. J. Org. Chem. 2004, 607–613.
Frank, M.; Maas, G.; Schatz, J. Eur. J. Org. Chem. 2006, 2378–2383.
Dinar`es, I.; Garcia de Miguel, C.; Font-Bardia, M.; Solans, X.; Alcalde, E. Organometallics 2007, 26, 5125–5128.
Brenner, E.; Matt, D.; Henrion, M.; Teci, M.; Toupet, L. Dalton Trans. 2011, 40, 9889–9898.
Fahlbusch, T.; Frank, M.; Schatz, J.; Sch¨uhle, D. T. J. Org. Chem. 2006, 71, 1688–1691.
Ren, H.; Xu, Y.; Jeanneau, E.; Bonnamour, I.; Tu, T.; Darbost, U. Tetrahedron 2014, 70, 2829–2837.
Reetz, M. T.; Kostas, I. D.; Waldvogel, S. R. Inorg. Chem. Commun. 2002, 5, 252–254.
Engeldinger, E.; Poorters, L.; Armspach, D.; Matt, D.; Toupet, L. Chem. Commun. 2004, 634–635.
Legrand, F. X.; Six, N.; Slomianny, C.; Bricout, H.; Tilloy, S.; Monflier, E. Adv. Synth. Catal. 2011, 353, 1325–1334.
Tran, D. N.; Legrand, F. X.; Menuel, S.; Bricout, H.; Tilloy, S.; Monflier, E. Chem. Commun. 2012, 48, 753–755.
Armspach, D.; Matt, D. Chem. Commun. 1999, 1073–1074.
Engeldinger, E.; Armspach, D.; Matt, D. Angew. Chem. Int. Ed. 2001, 40, 2526–2529.
Wong, Y. T.; Yang, C.; Ying, K. C.; Ji, G. Organometallics 2002, 21, 1782–1787.
Engeldinger, E.; Armspach, D.; Matt, D.; Jones, P. G.; Welter, R. Angew. Chem. Int. Ed. 2002, 41, 2593–2596.
Poorters, L.; Armspach, D.; Matt, D.; Toupet, L.; Choua, S.; Turek, P. Chem. Eur. J. 2007, 13, 9448–9461.
Guieu, S.; Zaborova, E.; Bl´eriot, Y.; Poli, G.; Jutand, A.; Madec, D.; Prestat, G.; Sollogoub, M. Angew. Chem. Int. Ed. 2010, 49, 2314–2318.
Poorters, L.; Armspach, D.; Matt, D.; Toupet, L. Dalton Trans. 2007, 3195–3202.
Gibson, C.; Rebek, J. Org. Lett. 2002, 4, 1887–1890.
Ta¸skıran, D. T.; Dumoulin, F.; Ahsen, V.; ˙I¸sci, ¨U. Dalton Trans. 2014, 43, 2032–2037.
Huang, W.; Guo, J.; Xiao, Y.; Zhu, M.; Zou, G.; Tang, J. Tetrahedron 2005, 61, 9783–9790.
Patil, S.; Deally, A.; Gleeson, B.; M¨uller-Bunz, H.; Paradisi, F.; Tacke, M. Metallomics 2011, 3, 74–88.
Bruker. APEX2, Version 2013.10-0. Bruker AXS Inc.: Madison, WI, USA, 2014.
Bruker. SAINT, Version 8.34A. Bruker AXS Inc.: Madison, WI, USA, 2013.
Bruker. SADABS, Version v2014/2. Bruker AXS Inc.: Madison, WI, USA, 2014.
Agilent Technologies. CrysAlisPRO, Version 1.171.37.31 (Release 14-01-2014 CrysAlis171 .NET). Agilent Tech- nologies: Santa Clara, CA, USA, 2011).
Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Spagna, R. J. Appl. Cryst. 2005, 38, 381–388.
Betteridge, P. W.; Carruthers, J. R.; Cooper, R. I.; Prout, K.; Watkin, D. J. J. Appl. Cryst. 2003, 36, 1487.
Spek, A. L. Acta Cryst. D 2009, 65, 148–155.
Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Cryst. 2006, 39, 453–457.
Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 2nd ed.; Pergamon Press: Oxford, UK, ¨ Ozdemir, ˙I.; S¸ahin, N.; G¨ok, Y.; Demir, S.; C¸ etinkaya, B. J. Mol. Catal. A-Chem. 2005, 234, 181–185.