An efficient microwave-assisted Suzuki reaction using Pd/MCM-41 and Pd/SBA-15 as catalysts in solvent-free condition

Wonghil Chang; GeumHee Chae; So Ra Jang; Jihye Shin; Byoung Joon Ahn

Journal of Industrial and Engineering Chemistry, Vol.18, No.2, 581-585, March, 2012

DOI10.1016/j.jiec.2011.11.043 Export Citation

An efficient microwave-assisted Suzuki reaction using Pd/MCM-41 and Pd/SBA-15 as catalysts in solvent-free condition

Wonghil Chang^†, GeumHee Chae¹, So Ra Jang¹, Jihye Shin, and Byoung Joon Ahn^{1, †}

Department of Basic Medical Science and EM R&D Center, Jeonju University, Jeonju 560-759, Republic of Korea
¹Department of Chemistry Education, Institute of Fusion Science, Institute of Science Education, Chonbuk National University, Jeonju 561-756, Republic of Korea

E-mail:,

Palladium catalysts, Pd/MCM-41 and Pd/SBA-15 were prepared by impregnation of an aqueous solution of [Pd(NH3)4]Cl2 on MCM-41 and SBA-15. Palladium contents of Pd/MCM-41 and Pd/SBA-15 are 8.4% and 8.7%, respectively. It has been shown that these catalysts are very suitable to microwave-assisted Suzuki reactions under solvent-free condition. It is also found that the base additives for this reaction are K2CO3, Cs2CO3 or CsF. Thus, phenylboronic acid and phenyl iodide with Pd/MCM-41 produce biphenyl by microwave irradiation for 10 min in 97.4% yield. Phenyl bromide, instead of phenyl iodide, also proceeds the reaction with phenylboronic acid using Pd/MCM-41 or Pd/SBA-15 yielding biphenyl by microwave irradiation for 10 min in excellent yield. Whereas the reaction of phenyl chloride with phenylboronic acid gives poor yield in same condition. Various aryl iodides and aryl bromides are tested. In this paper our recent results of microwave-assisted Suzuki reaction using Pd/MCM-41 and Pd/SBA-15 under solventfree condition are described.

Keywords:Microwave;Suzuki reaction;Pd/MCM-41;Pd/SBA-15;Solvent-free

[References]

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Artok L, Bulut H, Bulut H, Tetrahedron Lett., 45, 3881 (2004)
Artok L, Yilmaz S, Tetrahedron Lett., 44, 289 (2003)
Durgun G, Aksin O, Artok L, J. Mol. Catal. A-Chem., 278(1-2), 189 (2007)
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Jana S, Haldar S, Koner S, Tetrahedron Lett., 50, 4820 (2009)
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Namboodiri VV, Varma RS, Green Chem., 3, 146 (2001)
Wang JX, Yang Y, Wei B, Synth. Commun., 34, 2063 (2004)
Chang W, Shin J, Oh YH, Ahn BJ, J. Ind. Eng. Chem., 14(4), 423 (2008)
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[Referenced By]

[1] Alonso F, Beletskaya IP, Yus M, Tetrahedron., 61, 11771 (2005)

[2] Alonso F, Beletskaya IP, Yus M, Tetrahedron., 64, 3047 (2008)

[3] Liu SF, Xiao JL, J. Mol. Catal. A-Chem., 270(1-2), 1 (2007)

[4] Suzuki A, J. Organomet. Chem., 576, 147 (1999)

[5] Miyaura N, Suzuki A, Chem. Rev., 95, 133 (1995)

[6] Cepanec I, Synthesis of Biaryls, Elsevier, Amsterdam (2004)

[7] Yin LX, Liebscher J, Chem. Rev., 107(1), 133 (2007)

[8] Corbet JP, Mignani G, Chem. Rev., 106(7), 2651 (2006)

[9] Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M, Chem. Rev., 102(5), 1359 (2002)

[10] Augustine RL, Heterogeneous Catalysis for the Synthetic Chemist, Marcel Dekker, New York (1996)

[11] Artok L, Bulut H, Bulut H, Tetrahedron Lett., 45, 3881 (2004)

[12] Artok L, Yilmaz S, Tetrahedron Lett., 44, 289 (2003)

[13] Durgun G, Aksin O, Artok L, J. Mol. Catal. A-Chem., 278(1-2), 189 (2007)

[14] Han P, Wang XM, Qiu XP, Ji XL, Gao LX, J. Mol. Catal. A-Chem., 272(1-2), 136 (2007)

[15] Jana S, Haldar S, Koner S, Tetrahedron Lett., 50, 4820 (2009)

[16] Polshettiwar V, Len C, Fihri A, Coord. Chem. Rev., 253, 2599 (2009)

[17] Kosslick H, Monnich I, Paetzold E, Fuhrmann H, Fricke R, Muller D, Oehme G, Microporous Mesoporous Mater., 44, 537 (2001)

[18] Anastas PT, Warner JC, Green Chemistry: Theory and Practice, Oxford University Press, New York (1998)

[19] Tundo P, Anastas PT (Eds.), Green Chemistry: Challenging Perspectives, Oxford University Press, New York (2000)

[20] Tanaka K, Solvent-free Organic Synthesis, Wiely-VCH, Weinheim (2003)

[21] Namboodiri VV, Varma RS, Green Chem., 3, 146 (2001)

[22] Wang JX, Yang Y, Wei B, Synth. Commun., 34, 2063 (2004)

[23] Chang W, Shin J, Oh YH, Ahn BJ, J. Ind. Eng. Chem., 14(4), 423 (2008)

[24] Lee SK, Lee J, Joo J, Hyeon T, Ahn WS, Lee HI, Lee CH, Choi W, J. Ind. Eng. Chem., 9(1), 83 (2003)

[25] Ku HJ, Ahn BJ, Jeon BE, Chang W, J. Ind. Eng. Chem., 11(6), 841 (2005)

[26] Simeon JP, Sowa JR, Jeon BE, Tetrahedron., 63, 12646 (2007)