Nanoparticulate palladium catalyst stabilized by supported on feather keratin for Suzuki coupling reaction

doi:10.1016/S1872-2067(11)60472-5

Abstract

Abstract:

Palladium nanoparticlessupported in afeather keratin matrix were efficient catalyst for the coupling reactions of aryl bromides with arylboronic acid in aqueous medium under mild reaction conditions. The biopolymer-based catalyst demonstrated excellent activity for substrates with a wide range of functional groups. The product biaryls were precipitated from the reaction mixture with good to excellent yields and purities. The catalyst was recovered from the reaction solution easily by simple filtration, and can be reused at least seven times.

Key words: Suzuki reaction, Nanoparticle, Feather keratin, Hydrophobic effect, Water

MA Hengchang, BAO Zhikang, HAN Guobin, YANG Ningning, XU Yufei, YANG Zengming, CAO Wei, MA Yuan. Nanoparticulate palladium catalyst stabilized by supported on feather keratin for Suzuki coupling reaction[J]. Chinese Journal of Catalysis, 2013, 34(3): 578-584.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(11)60472-5

https://www.cjcatal.com/EN/Y2013/V34/I3/578

References

[1] Schmid G.Chem Rev, 1992, 92: 1709

[2] Sun T, Seff K.Chem Rev, 1994, 94: 857

[3] Wen F, Zhang W, Wei G, Wang Y, Zhang J, Zhang M, Shi L.Chem Mater, 2008, 20: 2144

[4] Alonso DA, Najera C.Chem Soc Rev, 2010, 39: 2891

[5] Karbass N, Sans V, Garcia-Verdugo E, Burguete M, Luis SV. ChemCommun, 2006: 3095

[6] Ogasawara S, Kato S.J Am Chem Soc, 2010, 132: 4608

[7] Zheng Z, Li H, Liu T, Cao R.J Catal, 2010, 270: 268

[8] Kochkar H, Aouine M, Ghorbel A, BerhaultG.J Phys Chem C, 2011, 115: 11364

[9] Niu WX, Zhang L, Xu GB.ACS Nano, 2010, 4: 1987

[10] Crespo-Quesada M, Andanson JM, Yarulin A, Lim B K, Xia Y N,Kiwi-Minsker L.Langmuir, 2011, 27: 7909

[11] Karimi B, Akhavan PF.InorgChem, 2011, 50: 6063

[12] Wen F, Zhang W, Wei G, Wang Y, Zhang J, Zhang M, Shi L.Chem Mater, 2008, 20: 2144

[13] Yin MY, Yuan GL, Wu YQ, Huang MY, Jiang YY. J Mol Catal A, 1999, 147: 93

[14] Zhou DQ, He M, Zhang YH, Huang MY, Jiang YY.Polym Adv Technol, 2003, 14: 287

[15] Xu Y, Zhang L, Cui Y.J Appl Polym Science, 2008, 110: 2996

[16] Molna?rA?. Chem Rev, 2011, 111: 2251

[17] Gallon BJ, Kojima RW, Kaner RB, Diaconescu PL.Angew Chem, Int Ed, 2007, 46: 7251

[18] Cho JK, Najman R, Dean TW, Ichihara O, Muller C, Bradley M.J Am Chem Soc, 2006, 128: 6276

[19] Schweizer S, Becht JM, Le Drian C.Tetrahedron, 2010, 66: 765

[20] Nishio R, Sugiura M, Kobayashi S.ChemAsian J, 2007, 2: 983

[21] Zhang M, Zhang W.J Phys Chem C, 2008, 112: 6245

[22] Ohtaka A, Teratani T, Fujii R, Ikeshita K, Shimomura O, Nomura R.Chem Commun, 2009: 7188

[23] Kitade Y, Sako S, Tsutsui A, Monguchi Y, Maegawa T, SajikiH. AdvSynthCatal, 2010,352: 718

[24] Wen F, Zhang W, Wei G, Wang Y, Zhang J, Zhang M, Shi L.Chem Mater, 2008, 20: 2144

[25] Miyaura N, Suzuki A.Chem Rev, 1995, 95: 2457

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

[27] Kotha S, Lahiri K, Kashinath D.Tetrahedron, 2002, 58: 9633

[28] Franzen R, Xu Y.Can J Chem, 2005, 83: 266

[29] Miyaura N.Top Curr Chem, 2002, 219: 11

[30] Zhu M Y, Diao G W.J Phys Chem C, 2012,116: 1626

[31] Pérez-Lorenzo Moisés.J Phys ChemLett,2012,3: 167

[32] Hariprasad E, Radhakrishnan T P. ACS Catal,2012,2: 1179

[33] Kim M J, Park J C, Kim A, Park K H, Song H. Langmuir,2012,28: 6441

[34] Chtchigrovsky M, Lin Y, Ouchaou K, Chaumontet M, Robitzer M, Quignard F, Taran F. Chem Mater,2012,24: 1505

[35] Wu S, Ma H C, Jia X J, Zhong Y M, Lei Z Q. Tetrahedron, 2011, 67:250

[36] Spiridon I, Paduraru O M, Rudowski M, Kozlowski M, Darie R N.Ind Eng Chem Res,2012,51: 7279

[37] Yin J, Rastogi S, Terry A E, Popescu C.Biomacromolecules,2007,8: 800

[38] Hu C Y, Reddy N, Yan K, Yang Y Q.J Agric Food Chem,2011,59: 10517

[39] Ullah A, Vasanthan T, Bressler D, Elias A L, Wu J P. Biomacromolecules, 2011,12: 3826

[40] Jin E Q, Reddy N, Zhu Z F, Yang Y Q. J Agric Food Chem,2011,59: 1729

[41] Poole A J, Church J S, Huson M G. Biomacromolecules,2009,10: 1

[42] Li FY, Wang RM, He YF, Li XX, Song PF, Ying XC, Mao CW.J Control Release, 2011, 152: 92

[43] Wang RM, Li FY, Wang XJ, Li QF, He YF, Wang YB.Funct Mater Lett, 2010, 3: 213

[44] Park JC, Heo E J, Kim A, Kim M J, Park KH, Song H J.J Phys Chem C, 2011, 115: 15772

[45] Bedford R B, Singh V G, Walton R I, Williams R T, Davis S A.Chem Mater, 2005, 17: 701

[46] Zhang P, Weng Z H, Guo J, Wang C C.Chem Mater, 2011, 23: 5243

[47] Niembro S, Vallribera A, Moreno-Mañas M.New J Chem, 2008, 32: 94

[48] Lu F, Ruiz J, Astruc D.Tetrahedron Lett, 2004, 45: 9443

[49] Barder T E, Walker S D, Martinelli JR, Buchwald SL.JAm Chem Soc,2005, 127:4685

[50] Doucet H. Eur J Org Chem, 2008: 2013

[51] Kinzel T, Zhang Y, Buchwald S. L.JAm Chem Soc,2010, 132:14073

[52] Solodenko W,Schön U, Messinger J, Glinschert A, Kirschning A.Synlett, 2004, 10: 1699

[53] Soomro S S, Rohlich C, Kohlerb K.AdvSynth Catal, 2011, 353: 767

[54] Ruan J W, Xiao J L. Acc Chem Res, 2011, 44: 614

[55] Wei G, Zhang W, Wen F, Wang Y, Zhang M. J Phys Chem C, 2008, 112, 10827

[56] Chen W, Li P, Wang L.Tetrahedron, 2011, 67: 318

[57] Mohanty S, Suresh D, Balakrishna M S, Mague J T.Tetrahedron, 2008, 64: 240

[58] Leadbeater N E, Marco M. Org Lett, 2002, 4:2973

[59] Kim J H, Kim J W, Shokouhimehr M, Lee Y. J Org Chem, 2005, 70: 6714