Palladium-EDTA and palladium-EdteH4 catalyzed Heck coupling reactions in pure water
Palladium-catalyzed Heck coupling reactions of styrene with bromoarene derivatives are carried out under aerobic conditions in water using water-soluble N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine (EdteH4) and ethylenediaminetetraacetic acid disodium salt (Na2EDTA) as ligands. The effect of different bases, catalyst loading, and additives is also monitored. The olefination of bromoarenes with styrene affords the desired products in high yields. The Na2PdCl4-Na2EDTA precatalyst system is also used for the preparative scale (50.0 mmol) synthesis of 4-acetyl-trans-stilbene and 4-styrylbenzaldehyde without a noticeable decrease in the activity. Recycling studies on the Na2PdCl4 - Na2EDTA precatalyst system are also tested in the coupling of 4-bromoacetophenone with styrene.
Palladium-EDTA and palladium-EdteH4 catalyzed Heck coupling reactions in pure water
Palladium-catalyzed Heck coupling reactions of styrene with bromoarene derivatives are carried out under aerobic conditions in water using water-soluble N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine (EdteH4) and ethylenediaminetetraacetic acid disodium salt (Na2EDTA) as ligands. The effect of different bases, catalyst loading, and additives is also monitored. The olefination of bromoarenes with styrene affords the desired products in high yields. The Na2PdCl4-Na2EDTA precatalyst system is also used for the preparative scale (50.0 mmol) synthesis of 4-acetyl-trans-stilbene and 4-styrylbenzaldehyde without a noticeable decrease in the activity. Recycling studies on the Na2PdCl4 - Na2EDTA precatalyst system are also tested in the coupling of 4-bromoacetophenone with styrene.
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- Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
- Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320–2322.
- Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press: London, 1985.
- Moln´ ar, A. Chem. Rev. 2011, 111, 2251–2320.
- Polshettiwar, V.; Moln´ ar, ´ A. Tetrahedron 2007, 63, 6949–6976.
- Phan, N. T. S.; van der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609–679.
- Whitcombe, N. J.; Hii, K. K. M.; Gibson, S. E. Tetrahedron 2001, 57, 7449–7476.
- Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009–3066.
- Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725–748.
- Shaughnessy, K. H. Chem. Rev. 2009, 109, 643–710.
- Torborg, C.; Beller, M. Adv. Synth. Catal. 2009, 351, 3027–3043.
- Li, C. J. Chem. Rev. 2005, 105, 3095–3166.
- Cornils, B.; Herrmann, W. A. Aqueous-Phase Organometallic Catalysis: Concept and Applications, Wiley-VCH: Weinheim, 2004.
- Undstr¨ om, U. M. Chem. Rev. 2002, 102, 2751–2772.
- Li, C. J.; Chan, T.H. Organic Reactions in Aqueous Media, Wiley: New York, 1997.
- Velazquez, H. D.; Verpoort, F. Chem. Soc. Rev. 2012, 41, 7032–7060.
- Simon, M. O.; Li, C. J. Chem. Soc. Rev. 2012, 41, 1415–1427.
- Lamblin, M.; Nassar-Hardy, L.; Hierso, J. C.; Fouquet, E.; Felpin, F. X. Adv. Synth. Catal. 2010, 352, 33–79.
- Tang, Y. Q.; Chu, C. Y.; Zhu, L.; Qian, B.; Shao, L. X. Tetrahedron 2011, 67, 9479–9483.
- G¨ ulcemal, S.; Kahraman, S.; Daran, J. C.; C ¸ etinkaya, E.; C ¸ etinkaya, B. J. Organomet. Chem. 2009, 694, 3580– 35
- Li, F.; Hor, T. S. A. Adv. Synth. Catal. 2008, 350, 2391–2400.
- Alacid, E.; Najera, C. Eur. J. Org. Chem. 2008, 73, 3102–3106.
- Botella, L.; Najera, C. Tetrahedron Lett. 2004, 45, 1833–1836.
- Hou, J. J.; Yang, L. R.; Cui, X.L.; Wu, Y. J. Chin. J. Chem. 2003, 21, 717–719.
- Iranpoor, N.; Firouzabadi, H.; Tarassoli, A.; Fereidoonnezhad, M. Tetrahedron 2010, 66, 2415–2421.
- Dawood, K. M. Tetrahedron 2007, 63, 9642–9651.
- Wu, S.; Ma, H.; Jia, X.; Zhong, Y.; Lei, Z. Tetrahedron 2011, 67, 250–256.
- Gil-Molt´ o, J.; Karlstr¨ om, S.; N´ ajera, C. Tetrahedron, 2005, 61, 12168-12176.
- Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami, S. Tetrahedron 2004, 60, 4097–4105.
- Cotugno, P.; Monopoli, A.; Ciminale, F.; Cioffi, N.; Nacci, A. Org. Biomol. Chem. 2012, 10, 808–813.
- Mondal, J.; Modak, A.; Bhaumik, A. J. Mol. Catal. A 2011, 350, 40–48.
- Shi, X.; Han, X.; Ma, W.; Fan, J.; Wei, J. Appl. Organomet. Chem. 2012, 26, 16–20.
- Wei, J.; Fu, H. Y.; Li, R. X.; Chen, H.; Li, X. L. Catal. Commun. 2011, 12, 748–752.
- Korolev, D. N.; Bumagin, N. A. Tetrahedron Lett. 2005, 46, 5751–5754.
- G¨ ulcemal, S.; Kani, ˙I.; Yılmaz, F.; C ¸ etinkaya, B. Tetrahedron 2010, 66, 5602–5606.
- Li, S.; Lin, Y.; Cao, J.; Zhang, S. J. Org. Chem. 2007, 72, 4067–4072.
- Li, J. H.; Liu, W. J.; Xie, Y. X. J. Org. Chem. 2005, 70, 5409–5412.
- Bernini, R.; Cacchi, S.; Fabrizi, G.; Forte, G.; Petrucci, F.; Prastaro, A.; Niembro, S.; Shafir, A.; Vallribera, A. Green Chem. 2010, 12, 150–158.
- Islam, M.; Mondal, P.; Roy, A. S.; Tuhina, K. Transition Met. Chem. 2010, 35, 491–499.
- Firouzabadi, H.; Iranpoor, N.; Gholinejad, M. Tetrahedron 2009, 65, 7079–7084.
- Choi, M.; Lee, D. H.; Na, K.; Yu, B. W.; Ryoo, R. Angew. Chem. Int. Ed. 2009, 48, 3673–3676.
- Wan, Q. X.; Liu, Y. Catal. Lett. 2009, 128, 487–492.
- Borhade, S. R.; Waghmode, S. B. Tetrahedron Lett. 2008, 49, 3423–3429.
- Likhar, P. R.; Roy, M.; Roy, S.; Subhas, M. S.; Kantam, M. L. Sreedhar, B. Adv. Synth. Catal. 2008, 350, 1968– 19
- Chen, W.; Li, R.; Han, B.; Li, B. J.; Chen, Y.C.; Wu, Y.; Ding, L. S.; Yang, D. Eur. J. Org. Chem. 2006, 1177–1184. Xiong, Z.; Wang, N.; Dai, M.; Li, A.; Chen, J.; Yang, Z. Org. Lett., 2004, 6, 3337–3340.
- Liu, J.; Zhao, Y.; Zhou, Y.; Li, L. Zhang, T. Y.; Zhang, H. Org. Biomol. Chem. 2003, 1, 3227–3231.
- Herrmann, W. A.; B¨ ohm, V. P. W.; Reisinger, C. P. J. Organomet. Chem. 1999, 576, 23–41.
- Louie, J.; Hartwig, J. F. Angew. Chem. Int. Ed. Engl. 1996, 35, 2359–2361.
- B¨ ohm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2001, 7, 4191–4197.
- Sundermann, A.; Uzan, O.; Martin, J. M. L. Chem. Eur. J. 2001, 7, 1703–1711.
- Sumimoto, M.; Kuroda, T.; Yokogawa, D.; Yamamoto, H.; Hori, K. J. Organomet. Chem. 2012, 710, 26–35.
- Yin, L.; Liebscher, J. Chem. Rev. 2007, 107, 133–173.
- Astruc, D. Inorg. Chem. 2007, 46, 1884–1894.
- Dietrich, S.; Nicolai, A.; Lang, H. J. Organomet. Chem. 2011, 696, 739-744.
- Cypryk, M.; Pospiech, P.; Strzelec, K.; Wasikowska, K.; Sobczac, J. W. J. Mol. Catal. A 2010, 319, 30–38.
- Widegren, J. A.; Finke, R. G. J. Mol. Catal. A 2003, 198, 317–341.
- Ott, L. S.; Finke, R. G. Coord. Chem. Rev. 2007, 251, 1075–1100.