Copper-free Sonogashira cross-coupling reactions catalyzed by an efficient dimeric C,N-palladacycle in DMF/H$_{2}$O
Very small concentrations of a dimeric C,N-palladacycle were used as an efficient homogeneous catalyst for Sonogashira cross-coupling reactions between various aryl halides and phenylacetylene. The catalytic reactions were performed without the need for copper in DMF/H$_{2}$O. This catalytic system shows excellent yields for aryl iodides and bromides and even in the case of aryl chlorides. \vs{1mm}
Copper-free Sonogashira cross-coupling reactions catalyzed by an efficient dimeric C,N-palladacycle in DMF/H$_{2}$O
Very small concentrations of a dimeric C,N-palladacycle were used as an efficient homogeneous catalyst for Sonogashira cross-coupling reactions between various aryl halides and phenylacetylene. The catalytic reactions were performed without the need for copper in DMF/H$_{2}$O. This catalytic system shows excellent yields for aryl iodides and bromides and even in the case of aryl chlorides. \vs{1mm}
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- Dupont, J.; Pfeffer, M. Palladacycles: Synthesis, Characterization and Applications; Wiley-VCH: Weinheim, Ger- many, 2008.
- Lloyd, L. Handbook of Industrial Catalysts, Fundamental and Applied Catalysis; Twigg, M. V.; Spencer, M. S., Eds. Springer: New York, NY, USA, 2011.
- Karami, K.; Ghasemi, M.; Haghighat Naeini, N. Catal. Commun. 2013, 38, 10–15.
- Buey, J.; Espinet, P. J. Organomet. Chem. 1996, 507, 137–145.
- Ghedini, M.; Aiello, I.; Crispini, A.; Golemme, A.; Deda, M. L.; Pucci, D. Coord. Chem. Rev. 2006, 250, 1373–1390.
- Garrett, C. E.; Prasad, K. Adv. Synth. Catal. 2004, 346, 889–900.
- Karami, K.; Karami Moghadam, Z.; Hosseini-Kharat, M. Cat. Commun. 2014, 43, 25–28.
- Beletskaya, I. P.; Cheprakov, A. V. J. Organomet. Chem. 2004, 689, 4055–4082.
- Karami, K.; Ghasemi, M.; Haghighat Naeini, N. Tetrahedron Lett. 2013, 54, 1352–1355.
- Ryabukhin, D. S.; Sorokoumov, V. N.; Savicheva, E. A.; Boyarskiy, V. P.; Balova, I. A.; Vasilyev, A. V. Tetrahedron Lett. 2013, 54, 2369–2372.
- Karami, K.; Bahrami Shehni, M.; Rahimi, N. Appl. Organomet. Chem. 2013, 27, 437–443.
- Alonso, D. A.; Najera, C.; Pacheco, M. C. J. Org. Chem. 2002, 67, 5588–5594.
- Alonso, D. A.; Najera, C.; Pacheco, M. C. Adv. Synth. Catal. 2002, 344, 172–183.
- Weissman, H.; Milstein, D. Chem. Commun. 1999, 1901–1902.
- Lamande-Langle, S.; Abarbri, M.; Thibonnet, J.; Duchene, A.; Parrain, J. L. Chem. Commun. 2010, 46, 5157–5159.
- Lin, B. N.; Huang, S. H.; Wu, W. Y.; Mou, C. Y.; Tsai, F. Y. Molecules 2010, 15, 9157–9173.
- Garg, N. K.; Woodroofe, C. C.; Lacenere, C. J.; Quake, S. R.; Stoltz, B. M. Chem. Commun. 2005, 36, 4551–4553.
- Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874–922.
- Chinchilla, R.; Najera, C. Chem. Rev. 2014, 114, 1783–1826.
- Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2, 422–424.
- Sindhu, K. S.; Anilkumar, G. RSC Adv. 2014, 4, 27867–27887.
- Bahramian, B.; Bakherad, M.; Keivanloo, A.; Bakherad, Z.; Karrabi, B. Appl. Organomet. Chem. 2011, 25, 420–
- Guan, J. T.; Weng, T. Q.; Yu, J. A.; Liu, S. H. Tetrahedron Lett. 2007, 48, 7129–7133.
- Alajarin, M.; Lopez-Leonardo, C.; Llamas-Lorente, P.; Raja, R.; Bautista, D.; Orenes, R. A. Dalton Trans. 2012, , 12259–12269.
- Yi, T.; Mo, M.; Fu, H. Y.; Fu, R. X.; Chen, H.; Li, X. J. Catal. Lett. 2012, 142, 594–600.
- Torborg, C.; Huang, J.; Schulz, T.; Schaffner, B.; Zapf, A.; Spannenberg, A.; Borner, A.; Beller, M. Chem. Eur. J. 2009, 15, 1329–1336.
- Choy, P. Y.; Chow, W. K.; So, C. M.; Lau, C. P.; Kwong, F. Y. Chem. Eur. J. 2010, 16, 9982–9985.
- Ngassa, F. N.; Gomez, J. M.; Haines, B. E.; Ostach, M. J.; Hector, J. W.; Hoogenboom, L. J.; Page, C. E. Tetrahedron 2010, 40, 7919–7926.
- Alonso, D. A.; Najera, C.; Pacheco, M. C. Tetrahedron Lett. 2002, 43, 9365–9368.
- Alacid, E.; Alonso, D, A.; Botella, L.; Najera, C.; Pacheco, M. C. Chem. Record. 2006, 6, 117–132.
- Blaszczyk, I.; Gniewek, A.; Trzeciak, A. M. J. Organomet. Chem. 2011, 696, 3601–3607.
- Susanto, W.; Chu, C. Y.; Ang, W. J.; Chou, T. C.; Lo, L. C.; Lam, Y. J. Org. Chem. 2012, 77, 2729–2742.
- Fortman, G. C.; Nolan, S. P. Chem. Soc. Rev. 2011, 40, 5151–5169.
- Yang, L. G.; Guan, P.; He, P.; Chen, Q.; Cao, C. S.; Peng, Y.; Shi, Z.; Pang, G. S.; Shi, Y. H. Dalton Trans. 2012, , 5020–5025.
- Ray, L.; Barman, S.; Shaikh, M. M.; Ghosh, P. Chem. Eur. J. 2008, 14, 6646–6655.
- Samantaray, M. K.; Shaikh, M. M.; Ghosh, P. J. Organomet. Chem. 2009, 694, 3477–3486.
- He, Y.; Cai, C. J. Organomet. Chem. 2011, 696, 2689–2692.
- Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047–1062.
- Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176–4211.
- Karami, K.; Rahimi, N.; Bahrami Shehni, M. Tetrahedron Lett. 2012, 53, 2428–2431.
- Kostas, I. D.; Steele, B .R.; Terzis, A.; Amosova, S. V. Tetrahedron 2003, 59, 3467–3473.
- Hajipour, A. R.; Karami, K.; Pirisedigh, A.; Ruoho, A. E. J. Organomet. Chem. 2009, 694, 2548–2554.
- Karami, K.; Haghighat Naeini, N. Appl. Organomet. Chem. 2015, 29, 33–39.
- Inomata, S.; Hiroki, H.; Terashima, T.; Ogata, K.; Fukuzawa, S. Tetrahedron 2011, 67, 7263–7267.
- Liang, Y.; Xie, Y. X.; Li, J. H. J. Org. Chem. 2006, 71, 379–381.
- Zhang, B. S.; Wang, C.; Gong, J. F.; Song, M. P. J. Organomet. Chem. 2009, 694, 2555–2561.
- Dash, C.; Shaikh, M. M.; Ghosh, P. Eur. J. Inorg. Chem. 2009, 2009, 1608–1941.
- Liang, B.; Dai, M.; Chen, J.; Yang, Z. J. Org. Chem. 2005, 70, 391–393.
- Alonso, D. A.; Najera, C.; Pacheco, M. C. Org. Lett. 2000, 2, 1823–1826.
- Baghbanian, S. M.; Yadollahy, H.; Tajbakhsh, M.; Farhang, M.; Biparva, P. RSC Adv. 2014, 4, 62532–62543.
- Gieshoff, T. N.; Welther, A.; Kessler, M. T.; Prechtl, M. H. G.; Jacobi von Wangelin, A. Chem. Commun. 2014, , 2261–2264.
- Gallop, C. W. D.; Chen, M. T.; Navarro, O. Org. Lett. 2014, 16, 3724–3727.
- Elangovan, A.; Wang, Y. H.; Ho, T. I. Org. Lett. 2003, 5, 1841–1844.
- Djakovitch, L.; Rollet, P. Adv. Synth. Catal. 2004, 346, 1782–1792.
- Wu, X. F.; Neumann, H.; Beller, M. Chem. Commun. 2011, 47, 7959–7961.