Application of the IB Group Nanoparticles in Organic Synthesis

doi:10.6023/cjoc201209005

Abstract

In recent years, there has been a great interest in using nanoparticles as catalysts in organic reactions. Because of their easy preparation and being relative stable in air, the nanoparticles of coinage metals such as copper, silver, and gold were widely reported, and there are many excellent examples on their applications as catalysts in the construction of carbon-carbon bond or carbon-hetero bond. Herein, the recent progress in the application of the group IB nanoparticles in organic synthesis is reviewed, and an outlook of their developments is also presented.

Key words: IB group nanoparticle, catalysis, organic synthesis

Cite this article

Yu Min, Han Chengyan, Wang Yong, Zhu Li, Yao Xiaoquan. Application of the IB Group Nanoparticles in Organic Synthesis[J]. Chin. J. Org. Chem., 2013, 33(03): 492-503.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice, Oxford University Press, New York, 2000.

[2] (a) Kidwai, M.; Bansal, V.; Saxena, A.; Aerry, S.; Mozumdar, S. Tetrahedron Lett. 2006, 47, 8049.
(b) Li, J. H.; Tang, B. X.; Tao, L. M.; Liang, Y.; Zhang, M. B. J. Org. Chem. 2006, 71, 7488.
(c) Tang, B. X.; Wang, F.; Li, J. H.; Xie, Y. X.; Zhang, M. B. J. Org. Chem. 2007, 72, 6294.
(d) Somorjai, G. A.; Materer, N. Top Catal. 1994, 1, 215.
(e) Thathagar, M. B.; Beckers, J.; Rothenberg, G. J. Am. Chem. Soc. 2002, 124, 11858.

[3] (a) Tan, Y.; Li, Y.; Zhu, D. J. Colloid Interface Sci. 2003, 258, 244.
(b) Sun, L.; Zhang, Z.; Dang, H. Mater. Lett. 2003, 57, 3874.
(c) Sondi, I.; Goia, D. V.; Matijevic, E. J. Colloid Interface Sci. 2003, 260, 75.
(d) Wiley, B.; Sun, Y.; Mayers, B.; Xia, Y. Chem. Eur. J. 2005, 11, 454.

[4] Ang, T. P.; Wee, T. S. A.; Chin, W. S. J. Phys. Chem. B 2004, 108, 11001.

[5] Kashiwagi, Y.; Yamamoto, M.; Nakamoto, M. J. Colloid Interface Sci. 2006, 300, 169.

[6] Solanki, J. N.; Sengupta, R.; Murthy, Z. V. P. Solid State Sci. 2010, 12, 1560.

[7] Yin, B. S.; Ma, H. Y.; Wang, S. Y. J. Phys. Chem. B 2003, 107, 8898.

[8] Hea, B.; Tanb, J. J.; Liewa, K. Y. J. Mol. Catal. A: Chem. 2004, 221, 121.

[9] Cozzoli, P. D.; Comparelli, R.; Fanizza, E. J. Am. Chem. Soc. 2004, 126, 3868.

[10] Naik, R. R.; Stringer, S. J.; Agarwal, G.; Jones, S. E.; Stone, M. O. Nat. Mater. 2002, 1, 169.

[11] Mandal, S.; Rautaray, D.; Sastry, M. J. Mater. Chem. 2003, 13, 3002.

[12] Yang, J.; Zhang, Q. B.; Lee, J. Y.; Too, H. P. J. Colloid Interface Sci. 2007, 308, 157.

[13] Liu, S. Q.; Fan, X.; Huang, J. H.; Huang, K. L. J. Central South Univ. 2007, 38, 497.

[14] Takesue, M.; Tomura, T.; Yamada, M.; Hata, K.; Kuwamoto, S.; Yonezawa, T. J. Am. Chem. Soc. 2011, 133, 14164.

[15] Patil, R. S.; Kokate, M. R.; Salvi, P. P.; Kolekar, S. S. C. R. Chim. 2011, 14, 1122.

[16] Xiong, Y. L.; Luo, G. Q.; Chen, C. ; Yuan, H.; Shen, Q.; Li, M. T. Appl. Surf. Sci. 2012, 258, 5822.

[17] Sun Y.; Yin Y.; Mayers B. T.; Herricks, T.; Xia, Y. N. Chem. Mater. 2002, 14, 4736.

[18] Qin, Y. Q.; Ji, X. H.; Jing, J.; Liu, H.; Wu, H. L.; Yang, W. S. Colloids Surf., A 2010, 372, 172.

[19] (a) Bagwe, R. P.; Khilar, K. G. Langmuir 2000, 16, 905.
(b) Liz-Marzan, L. M.; Lado-Tourino, L. Langmuir 1996, 12, 3585.

[20](a) Wang, W.; Chen, X.; Efrima, S. J. Phys. Chem. B 1999, 103, 7238.
(b) Yang, N.; Aoki, K. J. Phys. Chem. B 2005, 109, 23911.

[21] Cliffel, D. E.; Zamborini, F. P.; Cross, S. M.; Murray, R. W. Langmuir 2000, 16, 9699.

[22] (a) Chaki, N. K.; Sndrik, S. G.; Sonawane, H. R.; Vijayamohanan, K. Chem. Commun. 2002, 76.
(b) Chen, M.; Feng, Y. G.; Wang, X.; Li, T. C.; Zhang, J. Y.; Qian, D. J. Langmuir 2007, 23, 5296.

[23] (a) Vigneshwaran, N.; Nachane, R. P.; Balasubramanya, R. H.; Vara darajan, P. V. Carbohydr. Res. 2006, 341, 2012.
(b) Raveendran, P.; Fu, J.; Wallen, S. L. J. Am. Chem. Soc. 2003, 125, 13940.

[24] Hasell, T.; Yang, J. X.; Wang, W. X.; Brown, P. D.; Howdle, S. M. Mater. Lett. 2007, 61, 4906.

[25] Song, Y.; Liang, G.; Zhang, Q. Rare Metal Mater. Eng. 2007, 36, 709.

[26] Zhang, Z. Q.; Patel, R. C.; Kothari, R.; Johnson, C. P.; Fribery, S. E.; Aikens, P. A. J. Phys. Chem. B 2000, 104, 1176.

[27] Zhu, Y. J.; Qian, Y. T.; Li, X. J. Chem. Commun. 1997, 12, 1081.

[28] Zhang, Z. P.; Han, M. Y. J. Mater. Chem. 2003, 13, 641.

[29] Tian, K. H.; Liu, C. L.; Yang, H. J.; Ren, X. Y. Colloids Surf., A2012, 397, 12.

[30] Li, J. J.; Liu, C. L.; Ren, X. Y.; Yang, H. J.; Yang, J. X.; Yong, H. Precious Met. 2011, 32, 19.

[31] Lan, X. Z.; Jin, Z. H.; Zhao, X. C.; Gou, L. F. Rare Metal Mater. Eng. 2003, 32, 50.

[32] Rostovtsev, V. V.; Green, L. G.; Fokin V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.

[33] Orgueira, H. A.; Fokas, D.; Isome, Y.; Chan, P. C.-M.; Baldino, C. M. Tetrahedron Lett. 2005, 46, 2911.

[34] Kantam, M. L.; Jaya, V. S.; Sreedhar, B.; Rao, M. M.; Choudary, B. M. J. Mol. Catal. A: Chem. 2006, 256, 273.

[35] Raut, D.; Wankhede, K.; Vaidya, V.; Bhilare, S.; Darwatkar, N.; Deorukhkar, A.; Trivedi, G.; Salunkhe, M. Catal. Commun. 2009, 10, 1240.

[36] Sarkar, A.; Mukherjee, T.; Kapoor, S. J. Phys. Chem. C 2008, 112, 3334.

[37] Sharghi, H.; Khalifeh, R.; Doroodmand, M. M. Adv. Synth. Catal. 2009, 351, 207.

[38] Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Adv. Synth. Catal. 2010, 352, 3208.

[39] Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Eur. J. Org. Chem. 2010, 1875.

[40] Pach髇, L. D.; Maarseveen, J. H.; Rothenberg, G. Adv. Synth. Catal. 2005, 347, 811.

[41] Kidwai, M.; Bansal, V.; Saxena, A.; Aerry, S.; Mozumdar, S. Tetrahedron Lett. 2006, 47, 8049.

[42] Kidwai, M.; Mishra, N. K.; Bansal, V.; Kumar, A.; Mozumdar, S. Tetrahedron Lett. 2009, 50, 1355.

[43] Verma, A. K.; Kumar, R.; Chaudhary, P.; Saxena, A.; Shankar, R.; Mozumdar, S.; Chandra, R. Tetrahedron Lett. 2005, 46, 5229.

[44] Ranu, B. C.; Saha, A.; Jana, R. Adv. Synth. Catal. 2007, 349, 2690.

[45] Son, S. U.; Park, I. K.; Park, J.; Hyeon, T. Chem. Commun. 2004, 778.

[46] Kidwai, M.; Bhardwaj, S.; Mishra, N. K.; Bansal, V.; Kumar, A.; Mozumdar, S. Catal. Commun. 2009, 10, 1514.

[47] Singh, P.; Katyal, A.; Kalra, R.; Chandra, R. Tetrahedron Lett. 2008, 49, 727.

[48] Thathagar, M. B.; Beckers, J.; Rothenberg, G. J. Am. Chem. Soc. 2002, 124, 11858.

[49] Kantam, M. L.; Jaya, V. S.; Lakshmi, M. J.; Reddy, B. R.; Choudary, B. M.; Bhargava, S. K. Catal. Commun. 2007, 8, 1963.

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

[51] Iyer, S.; Thakur, V. V. J. Mol. Catal. A: Chem. 2000, 157, 275.

[52] (a) Weibel, J. M.; Blanc, A.; Pale, P. Chem. Rev. 2008, 108, 3149.
(b) Naodovic, M.; Yamamoto, H. Chem. Rev. 2008, 108, 3132.
(c) Dias, H. V. R.; Lovely, C. J. Chem. Rev. 2008, 108, 3223.
(d) Yamamoto, Y. Chem. Rev. 2008, 108, 3199.
(e) 羖varez-Corral, M.; Muñoz-Dorado, M.; Rodr韌uez-Garc韆, I. Chem. Rev. 2008, 108, 3174.
(f) Halbes-Letinois, U.; Weibel, J.-M.; Pale, P. Chem. Soc. Rev. 2007, 36, 759.

[53] (a) Mitsudome, T.; Funai, H.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Angew. Chem., Int. Ed. 2008, 47, 138.
(b) Shimizu, K.; Sugino, K.; Sawabe, K.; Satsuma, A. Chem. Eur. J. 2009, 15, 2341.

[54] (a) Shin, K. S.; Choi, J.-Y.; Park, C. S.; Jang, H. J.; Kim, K. Catal. Lett. 2009, 133, 1.
(b) Brandt, K.; Chiu, M. E.; Watson, D. J.; Tikhov, M. S.; Lambert, R. M. J. Am. Chem. Soc. 2009, 131, 17286.
(c) Pradhan, N.; Pal, A.; Pal, T. Colloids Surf., A 2002, 196, 247.
(d) Pradhan, N.; Pal, A.; Pal, T. Langmuir 2001, 17, 1800.

[55] Li, Z.; Wei, C.; Chen, L.; Varma, R. S.; Li, C.-J. Tetrahedron Lett. 2004, 45, 2443.

[56] Yan, W.; Wang, R.; Xu, Z.; Xu, J.; Lin, L.; Shen, Z.; Zhou, Y. J. Mol. Catal. A: Chem. 2006, 255, 81.

[57] Wang, S.; He, X.; Song, L.; Wang, Z. Synlett 2009, 447.

[58] Yong, G. P.; Tian, D.; Tong, H. W.; Liu, S. M. J. Mol. Catal. A: Chem. 2010, 323, 40.

[59] (a) Harkat, H.; Blanc, A.; Weibel, J. M.; Pale, P. J. Org. Chem. 2008, 73, 1620.
(b) Yu, M.; Skouta, R.; Zhou, L.; Jiang, H. F.; Yao, X. Q.; Li, C.-J. J. Org. Chem. 2009, 74, 3378.
(c) Lin, M.; Yu, M.; Han, C.; Li, C. J.; Yao, X. Synth. Commun. 2011, 41, 3228.

[60] Yu, M.; Lin, M. D.; Han, C. Y.; Zhu, L.; Li, C. J.; Yao, X. Tetrahedron Lett. 2010, 51, 6722.

[61] Yu, M.; Wang, Y.; Sun, W. J.; Yao, X. Adv. Synth. Catal. 2012, 354, 71.

[62] Murugadoss, A.; Goswami, P.; Paul, A.; Chattopadhyay, A. J. Mol. Catal. A: Chem. 2009, 304, 153.

[63] Shimizu, K.; Sawabe, K.; Satsuma, A. Catal. Sci. Technol. 2011, 1, 331.

[64] Shimizu, K.; Sato, R.; Satsuma, A. Angew. Chem., Int. Ed. 2009, 48, 3982.

[65] Shimizu, K.; Ohshima, K.; Satsuma, A. Chem. Eur. J. 2009, 15, 9977.

[66] Shimizu, K.; Nishimura, M.; Satsuma, A. ChemCatChem 2009, 1, 497.

[67] Mitsudome, T.; Arita, S.; Mori, H.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Angew. Chem., Int. Ed. 2008, 47, 7938.

[68] Shimizu, K.; Miyamoto, Y.; Satsuma, A. ChemCatChem 2010, 2, 84.

[69] Carrettin, S.; Blanco, M. C.; Corma, A.; Hashmi, A. S. K. Adv. Synth. Catal. 2006, 348, 1283.

[70] Abad, A.; Corma, A.; Garc韆, H. Top. Catal. 2007, 44, 237.

[71] Ra, P.; Evangelisti, C.; Vitulli, G.; Salvadori, P. Tetrahedron Lett. 2008, 49, 3221.

[72] Raptis, C.; Garcia, H.; Stratakis, M. Angew. Chem., Int. Ed. 2009, 48, 3133.

[73] Chng, L. L.; Yang, J.; Wei, Y.; Ying, J. Y. Adv. Synth. Catal. 2009, 351, 2887.

[74] Kidwai, M.; Bansal, V.; Kumar, A.; Mozumdar, S. Green Chem. 2007, 9, 742.

[75] Kim, S.; Bae, S. W.; Lee, J. S.; Park, J. Tetrahedron 2009, 65, 1461.

[76] Souza, R. O. M. A.; Bittar, M. S.; Mendes, L. V. P.; Silva, C. M. F.; Silva, V. T.; Antunes, O. A. C. Synlett 2008, 1777.

[77] Chaicharoenwimolkul, L.; Munmai, A.; Chairam, S.; Tewasekson, U.; Sapudom, S.; Lakliang, Y.; Somsook, E. Tetrahedron Lett. 2008, 49, 7299.

[78] Ram韗ez, J.; Sana?, M.; Fern醤dez, E. Angew. Chem., Int. Ed. 2008, 47, 5194.

[79] Asao, N.; Ishikawa, Y.; Hatakeyama, N.; Menggenbateer; Yamamoto, Y.; Chen, M. W.; Zhang, W.; Inoue, A. Angew. Chem., Int. Ed. 2010, 49, 10093.

IB族金属纳米颗粒在有机合成反应中的应用