Montmorillonite Supported Pd/Cu Bimetallic Nanoparticle Catalyzed Sonogashira Coupling

doi:10.6023/cjoc201301077

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (04): 820-826.DOI: 10.6023/cjoc201301077 Previous Articles Next Articles

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蒙脱土负载Pd/Cu双金属纳米微粒催化Sonogashira偶联反应

徐伟, 孙原龙, 郭萌涵, 张伟强, 高子伟

陕西师范大学化学化工学院西安 710062

收稿日期:2013-01-29 修回日期:2013-03-18 发布日期:2013-03-22
通讯作者: 张伟强, 高子伟 E-mail:zwq@snnu.edu.cn, zwgao@snnu.edu.cn
基金资助:
国家自然科学基金(Nos. 21271124, 21041004, 20771071)、教育部新世纪优秀人才项目支持计划(No. NCET-07-0528)、中央高校基本业务费(Nos. GK201004010, GK201002031)及“春笋计划”(No. 2010-2011西安中学)资助项目.

Montmorillonite Supported Pd/Cu Bimetallic Nanoparticle Catalyzed Sonogashira Coupling

Xu Wei, Sun Yuanlong, Guo Menghan, Zhang Weiqiang, Gao Ziwei

School of Chemisty & Chemical Engineering, Shaanxi Normal University, Xi'an 710062

Received:2013-01-29 Revised:2013-03-18 Published:2013-03-22
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21271124, 21041004, 20771071), the Program for New Century Excellent Talents in University (No. NCET-07-0528), the Fundamental Research Funds for the Central Universities (Nos. GK201002031, GK201004010) and the Doctoral Fund of Ministry of Education of China (No. 20120202120005).

To demonstrate the bimetallic effect of transition metal catalyzed C—C cross coupling, the montmorillonite (MMT) supported mixed palladium and copper nanoparticles were prepared and applied to catalytic Sonogashira couplings. A new method of preparing mixed metal nanoparticles was invented based on unique metal ion adsorption capacity of montmorillonite and sequential reductive carbonylation via thermolysis of N,N-dimethylformide, and Pd/Cu bimetallic nanoparticals was prepared in the ratio of 1∶1. A mixed solvent system, dimethoxyethane/water (V∶V＝1∶4) was identified as the best solvent of the catalytic coupling. MMT@Pd/Cu catalyzed efficiently the cross-coupling of aryl iodides and terminal aryl- and alkyl-ynes in presence of potassium carbonate and triphenyl phosphine. 15 cross-coupling yne derivatives were isolated in excellent to moderate yields. Experimental kinetic study reveals that both swelling of montmorillonite promoted by water and Pd/Cu bimetallic synergistic effect play critical roles in high activity of the catalyst.

Key words: transition metal catalysis, montmorillonite, C—C cross-coupling, bimetallic effect

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Xu Wei, Sun Yuanlong, Guo Menghan, Zhang Weiqiang, Gao Ziwei. Montmorillonite Supported Pd/Cu Bimetallic Nanoparticle Catalyzed Sonogashira Coupling[J]. Chin. J. Org. Chem., 2013, 33(04): 820-826.

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[1] Balanta, A.; Godard, C.; Claver, C. Chem. Soc. Rev. 2011, 40, 4973.

[2] Chinchilla, R.; Najera, C. Chem. Soc. Rev. 2011, 40, 5084.

[3] Sanhes, D.; Raluy, E.; Retory, S.; Saffon, N.; Teuma, E.; Gomez, M. Dalton Trans. 2010, 39, 9719.

[4] Gao, S.; Zhao, N.; Shu, M.; Che, S. Appl. Catal. A-Gen. 2010, 388, 196.

[5] Pacardo, D. B.; Slocik, J. M.; Kirk, K. C.; Naik, R. R.; Knecht, M. R. Nanoscale 2011, 3, 2194.

[6] Ananikov, V. P.; Beletskaya, I. P. Organometallics 2012, 31, 1595.

[7] Heravi, M. M.; Sadjadi, S. Tetrahedron 2009, 65, 7761.

[8] Plenio, H. Angew. Chem., Int. Ed. 2008, 47, 6954.

[9] (a) Li, Y.; Zhou, P.; Dai, Z.; Hu, Z.; Sun, P.; Bao, J. New J. Chem. 2006, 30, 832.
(b) Li, H.; Zhu, Z.; Liu, J.; Xie, S.; Li, H. J. Mater. Chem. 2010, 20, 4366.

[10] Venkatesan, P.; Santhanalakshmi, J. Langmuir 2010, 26, 12225.

[11] Thathagar, M. B.; Beckers, J.; Rothenberg, G. Green Chem. 2004, 6, 215.

[12] B閦ier, D.; Darcel, C. Adv. Synth. Catal. 2009, 351, 1732.

[13] Taillefer, M.; Xia, N.; Ouali, A. Angew. Chem. 2007, 46, 934.

[14] Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. D. J. Org. Chem. 2005, 70, 161.

[15] Stefanescu, D. M.; Yuen, H. F.; Glueck, D. S.; Golen, J. A.; Rheingold, A. L. Angew. Chem., Int. Ed. 2003, 42, 1046.

[16] Bonnamour, J.; Piedrafita, M.; Bolm, C. Adv. Synth. Catal. 2010, 352, 1577.

[17] Fukino, T.; Fujita, N.; Aida, T. Org. Lett. 2010, 12, 3074.

[18] Correa, A.; Bolm, C. Adv. Synth. Catal. 2008, 350, 391.

[19] Thome, I.; Nijs, A.; Bolm, C. Chem. Soc. Rev. 2012, 41, 979.

[20] Buchwald, S. L.; Bolm, C. Angew. Chem. 2009, 121, 5694.

[21] Ranga Rao, G.; Mishra, B. G. J. Porous Mater. 2006, 14, 205.

[22] Mastalir, ?.; Kir醠y, Z.; Berger, F. Appl. Catal. A-Gen. 2004, 269, 161.

[23] Singh, V.; Ratti, R.; Kaur, S. J. Mol. Catal. A: Chem. 2011, 334, 13.

[24] Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993..

[25] Moore, D. R.; Cheng, M.; Lobkovsky, E. B.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2599.

[26] Kobayashi, S.; Endo, M.; Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229.

[27] Suzuki, A. J. Organomet. Chem. 1999, 576, 147.

[28] Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.

[29] Papp, A.; Mikl髎, K.; Forgo, P.; Moln醨, ?. J. Mol. Catal. A: Chem. 2005, 229, 107.

[30] Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057.

[31] Bedford, R. B.; Light, M. E.; Cazin, C. S.J.; Pike, K. J.; Hursthouse, M. B.; Wimperis, S. J. Organomet. Chem. 2001, 633, 173.

[32] Bulut, H.; Artoka, L.; Yilmazb, S. Tetrahedron Lett. 2003, 44, 289.

[33] Corma, A.; Garcia, H.; Leyva, A. Appl. Catal. A-Gen. 2002, 236, 179.

[34] Smith, M. D.; Stepan, A. F.; Ramarao, C.; Brennan, P. E.; Ley, S. V. Chem. Commun. 2003, 2652.

[35] Djakovitch, L.; Rollet, P. Adv. Synth. Catal. 2004, 346, 1782.

[36] Mehnert, C. P. Chem. Commun. 1997, 2215.

[37] Scheuermann, G. M.; Thomann, R.; M黮haupt, R. Catal. Lett. 2009, 132, 355.

[38] Motokura, K.; Fujita, N.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2005, 127, 9674.

[39] Mastalir, ?.; Kir醠y, Z.; Berger, F. Appl. Catal. A: Gen. 2004, 269, 161.

[40] De-la-Rosa, M. A.; Velarde, E.; Guzm醤, A. Synth. Commun. 1990, 20, 2059

[41] Potts, K. T.; Horwitz, C. P.; Fessak, A.; Keshavarz-K, M.; Nash, K. E.; Toscano, P. J. J. Am. Chem. Soc. 1993, 115, 10444.

[42] Hensen, E. J. M.; Smit, B. J. Phys. Chem. B 2002, 106, 12664.

[43] Powell, D. H.; Fischer, H. E.; Helm, L. J. Phys. Chem. B 1998, 102, 10899.

[44] Helmy, A. K. J. Colloid Interface Sci. 1998, 207, 128. Karaborni, S.; Smit, B.; Heidug, W.; Urai, J.; van Oort, E. Science 1996, 271, 1102.

蒙脱土负载Pd/Cu双金属纳米微粒催化Sonogashira偶联反应

Montmorillonite Supported Pd/Cu Bimetallic Nanoparticle Catalyzed Sonogashira Coupling

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