Synthesis of in-situ surfactant-free Pd nanoparticle catalysts for the synthesis of aromatic azo compounds and for unsaturated bond hydrogenation by hydrogen transfer

doi:10.1016/S1872-2067(12)60665-2

Abstract

Abstract:

We developed a simple and efficient method to synthesize aromatic azos by hydrogen transfer using palladium(Ⅱ) acetylacetonate as a catalyst and isopropyl alcohol as a hydrogen source. Furthermore, this system also showed catalytic potential for the hydrogenation of carbonyl groups or C=C bonds with yields up to ~97%.

Key words: Nanocatalyst, Palladium, Transfer hydrogenation, In-situ synthesis, Azo

Xin Wang, Jiaqing Wang, Fenqiang Qi, Lei Hu, Xinming Li, Xueqin Cao, Hongwei Gu. Synthesis of in-situ surfactant-free Pd nanoparticle catalysts for the synthesis of aromatic azo compounds and for unsaturated bond hydrogenation by hydrogen transfer[J]. Chinese Journal of Catalysis, 2013, 34(11): 2084-2088.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(12)60665-2

https://www.cjcatal.com/EN/Y2013/V34/I11/2084

References

[1] Brieger G, Nestrick T J. Chem Rev, 1974, 74: 567
[2] Johnstone R A W, Wilby A H, Entwistle I D. Chem Rev, 1985, 85: 129
[3] Zassinovich G, Mestroni G, Gladiali S. Chem Rev, 1992, 92: 1051
[4] Fujii A, Hashiguchi S, Uematsu N, Ikariya T, Noyori R. J Am Chem Soc, 1996, 118: 2521
[5] Noyori R, Hashiguchi S. Acc Chem Res, 1997, 30: 97
[6] Palmer M J, Wills M. Tetrahedron Asymmetry, 1999, 10: 2045
[7] Blaser H U, Malan C, Pugin B, Spindler F, Steiner H, Studer M. Adv Synth Catal, 2003, 345: 103
[8] Clapham S E, Hadzovic A, Morris R H. Coord Chem Rev, 2004, 248: 2201
[9] Gladiali S, Alberico E. Chem Soc Rev, 2006, 35: 226
[10] Samec J S M, Backvall J E, Andersson P G, Brandt P. Chem Soc Rev, 2006, 35: 237
[11] Ikariya T, Blacker A J. Acc Chem Res, 2007, 40: 1300
[12] Rhyoo H Y, Park H J, Suh W H, Chung Y K. Tetrahedron Lett, 2002, 43: 269
[13] Saluzzo C, Lemaire M. Adv Synth Catal, 2002, 344: 915
[14] Miecznikowski J R, Crabtree R H. Organometallics, 2004, 23: 629
[15] Baratta W, Chelucci G, Gladiali S, Siega K, Toniutti M, Zanette M, Zangrando E, Rigo P. Angew Chem Int Ed, 2005, 44: 6214
[16] Koike T, Ikariya T. Adv Synth Catal, 2004, 346: 37
[17] Rueping M, Sugiono E, Azap C. Theissmann T, Bolte M. Org Lett, 2005, 7: 3781
[18] Jagadeesh R V, Wienhoefer G, Westerhaus F A, Surkus A E, Junge H, Junge K, Beller M. Chem Eur J, 2011, 17: 14375
[19] Hoult J R S. Drugs, 1986, 32(Suppl 1): 18
[20] Stick R V, Mocerino M, Franz D A. J Chem Edu, 1996, 73: 540
[21] Orban M, Kurin-Csorgei K, Zhabotinsky A M, Epstein I R. J Am Chem Soc, 1998, 120: 1146
[22] Kuwabara T, Nakajima H, Nanasawa M, Ueno A. Anal Chem, 1999, 71: 2844
[23] Hunger K. Industrial Dyes: Chemistry, Properties, Applications. Weinheim: Wiley-VCH, 2003
[24] Srinivasa G R, Abiraj K, Gowda D C. Tetrahedron Lett, 2003, 44: 5835
[25] Moglie Y, Vitale C, Radivoy G. Tetrahedron Lett, 2008, 49: 1828
[26] Hu L, Cao X Q, Shi L Y, Qi F Q, Guo Z Q, Lu J M, Gu H W. Org Lett, 2011, 13: 5640
[27] Zhao R, Tan C Y, Xie Y H, Gao C M, Liu H X, Jiang Y Y. Tetrahedron Lett, 2011, 52: 3805
[28] Wenkert E, Wickberg B. J Am Chem Soc, 1962, 84: 4914
[29] Baumgarten H E, Staklis A, Miller E M. J Org Chem, 1965, 30: 1203
[30] Wenkert E, Angell E C. Synth Commun, 1988, 18: 1331
[31] Grirrane A, Corma A, Garcia H. Science, 2008, 322: 1661
[32] Grirrane A, Corma A, Garcia H. Nat Protoc, 2010, 5: 429
[33] Teng X W, Han W Q, Ku W, Huecker M. Angew Chem Int Ed, 2008, 47: 2055
[34] Huang X Q, Zheng N F. J Am Chem Soc, 2009, 131: 4602
[35] Yuan Q, Zhuang J, Wang X. Chem Commun, 2009: 6613
[36] Liang H W, Liu S, Gong J Y, Wang S B, Wang L, Yu S H. Adv Mater, 2009, 21: 1850
[37] Wang J J, Chen Y G, Liu H, Li R Y, Sun X L. Electrochem Commun, 2010, 12: 219
[38] Mondal M, Bora U. Green Chem, 2012, 14: 1873
[39] Kleist W, Proeckl S S, Koehler K. Catal Lett, 2008, 125: 197
[40] Dong J J, Roger J, Pozgan F, Doucet H. Green Chem, 2009, 11: 1832