Murat YİĞİT, Gülin BAYAM, Beyhan YİĞİT, İsmail ÖZDEMİR

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

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.

Anahtar Kelimeler:

Heck reaction, imidazolinium salt, palladium, N-heterocyclic carbene, catalyst

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

Keywords:

Heck reaction, imidazolinium salt, palladium, N-heterocyclic carbene, catalyst,

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Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320–2322.
Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press: London, UK, 1985.
Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945–2963.
Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10–11.
Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989–7000.
Feuerstein, M.; Doucet, H.; Santelli, M. J. Org. Chem. 2001, 66, 5923–5925.
Moore, L. R.; Shaughnessy, K. H. Org. Lett. 2004, 6, 225–228.
Ehrentraut, A.; Zapf, A.; Beller, M. Synlett 2000, 1589–1592.
Lee, D. H.; Taher, A.; Hossain, S.; Jin, M. J. Org. Lett. 2011, 13, 5540–5543.
Sabounchei, S. J.; Ahmedi, M.; Panahimehr, M.; Bagherjeri, F. A.; Nasri, Z. J. Mol. Catal. A: Chem. 2014, 383–384, 249–259.
Herrmann, W. A.; Reisinger, C. P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93–98.
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.
Lee, C. S.; Lai, Y. B.; Lin, W. J.; Zhuang, R. R.; Hwang, W. S. J. Organomet. Chem. 2013, 724, 235–243.
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.
Lai, Y. C.; Chen, H. Y.; Hung, W. C.; Lin, C. C.; Hong, F. E. Tetrahedron 2005, 61, 9484–9489.
Tao, B.; Boykin, D. W. Tetrahedron Lett. 2003, 44, 7993–7996.
Gossage, P. A.; Jenkins, H. A.; Yadav, P. N. Tetrahedron Lett. 2004, 45, 7689–7691.
Buncmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101–11107.
Iyer, S.; Kulkarni, G. M.; Ramesh, C. Tetrahedron 2004, 60, 2163–2172.
Mino, T.; Shirae, Y.; Sakamoto, M.; Fujita, T. J. Org. Chem. 2005, 70, 2191–2194.
Cui, X.; Zhou, Y.; Wang, N., Liu, L.; Guo, Q. X. Tetrahedron Lett. 2007, 48, 163–167.
Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2000, 46, 181–222.
Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290–1309.
Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2239–2246.
Viciu, M, S.; Kelly, R. A.; Stevens, E. D.; Naud, F.; Studer, M.; Nolan, S. P. Org. Lett. 2003, 5, 1479–1482.
Matsubara, K.; Ueno, K.; Koga, Y.; Hara, K. J. Org. Chem. 2007, 72, 5069–5076.
Trindade, A. F.; Gois, P. M. P.; Veiros, L. F.; Andre, V.; Duarte, M. T.; Afonso, C. A. M.; Caddick, S.; Cloke, F. G. N. J. Org. Chem. 2008, 73, 4076–4086.
Schaub, T.; Fischer, P.; Steffen, A.; Braun, T.; Radius, U.; Mix, A. J. Am. Chem. Soc. 2008, 130, 9304–9317.
He, M.; Bode, J. W. J. Am. Chem. Soc. 2008, 130, 418–419.
Matsumoto, Y.; Yamada, K.; Tomioka, A. J. Org. Chem. 2008, 73, 4578–4581.
Stauffer, S. R.; Lee, S.; Stambuli, J. F.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423–1426.
Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119–122.
Yigit, B.; Yi˘git, M.; ¨Ozdemir, ˙I.; C¸ etinkaya, E. Turk. J. Chem. 2010, 34, 327–334.
Yi˘git, B. Transition Metal Chem. 2012, 37, 183–188. ¨
Ozdemir, ˙I.; G¨ok, Y.; G¨urb¨uz, N.; C¸ etinkaya, B. Turk. J. Chem. 2007, 31, 397–402.
Yigit, B.; Yi˘git, M.; ¨Ozdemir, ˙I.; C¸ etinkaya, E. Heterocycles 2010, 81, 943–953.
Yigit, B.; Yi˘git, M.; ¨Ozdemir, ˙I.; C¸ etinkaya, E. Heterocycles 2011, 83, 299–309.
C¸ etinkaya, E.; Hitchcock, P. P.; Jasim, H. A.; Lappert, M. F.; Spyropoulos, K. J. Perkin Trans. 1. 1992, 561–567.
Saba, S.; Brescia, A.; Kaloustian, M. K. Tetrahedron Lett. 1991, 32, 5031–5034.
Arduengo, III, A. J.; Krafczyk, R.; Schmutzler, R. Tetrahedron 1999, 55, 14523–14534.
Marshall, C.; Ward, M. F.; Harrison, W. T. A. J. Organomet. Chem. 2005, 690, 3970–3975.
Arnold, P. L.; Pearson, S. Coord. Chem. Rev. 2007, 251, 596–609.
Corberan, R.; Sanau, M.; Peris, E. Organometallic 2007, 26, 3492–3498.
Yi˘git, M.; ¨Ozdemir, ˙I.; C¸ etinkaya, E.; C¸ etinkaya, B. Heteroatom Chem. 2005, 16, 461–465.
Ozdemir, ˙I.; Yi˘git, M.; C¸ etinkaya, E.; C¸ etinkaya, B. Heterocycles 2006, 68, 1371–1379. ¨
Yi˘git, M., ¨Ozdemir, ˙I.; C¸ etinkaya, B.; C¸ etinkaya, E. J. Mol. Catal. A: Chem. 2005, 241, 88–92.
Ogle, J. W.; Zhang, J.; Reibenspies, J. H.; Abboud, K. A.; Miller, S. A. Org. Lett. 2008, 10, 3677–3680.
Hadei, N.; Kantchev, E. A. B.; O’Brien, C. J.; Organ, M. G. Org. Lett. 2005, 7, 1991–1994.
Baratta, W.; Sch¨utz, J.; Herdtweck, E.; Herrmann, W. A.; Rigo, P. J. Organomet. Chem. 2005, 690, 5570–5575.
T¨urkmen, H.; C¸ etinkaya, B. J. Organomet. Chem. 2006, 691, 3749–3759.
G¨ulcemal, S.; Kahraman, S.; Daran, J. C.; C¸ etinkaya, E.; C¸ etinkaya, B. J. Organomet. Chem. 2009, 694, 3580– 35
Rajabi, F.; Trampert, J.; Sun, Y.; Busch, M.; Brase, S.; Thiel, W. R. J. Organomet. Chem. 2013, 744, 101–107.