Microwave-assisted Sonogashira cross-coupling reaction catalyzed by Pd-MCM-41 under solvent-free conditions

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

Journal of Industrial and Engineering Chemistry, Vol.19, No.3, 739-743, May, 2013

DOI10.1016/j.jiec.2012.11.002 Export Citation

Microwave-assisted Sonogashira cross-coupling reaction catalyzed by Pd-MCM-41 under solvent-free conditions

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

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

E-mail:,

In this paper microwave-assisted Sonogashira reactions of phenyl acetylene with aryl iodide using palladium modified Pd-MCM-41, Pd-Y, Pd-VSB-5 and Pd-SBA-15 under solvent-free conditions were described. The results of microwave-assisted Sonogashira reaction using Pd-MCM-41 or Pd-Y in aqueous conditions were also discussed. The microwave-assisted reaction of phenyl acetylene with phenyl iodide using Pd-Y or Pd-MCM-41 and DBU as a base under solvent-free conditions resulted in yields of 85% and 93%, respectively. The reaction with Pd-Y or Pd-MCM-41 using DBU in DMF:H2O (4:1) solution reduced yields to 64% and 76%, respectively.

Keywords:Microwave-assisted;Sonogashira reaction;Pd-MCM-41;Solvent-free;Green chemistry

[References]

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de Meijere A, Diederich F (Eds.), Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim (2004)
Polshettiwar V, Len C, Fihri A, Coordination Chemistry Reviews., 253, 2599 (2009)
Alonso F, Beletskaya IP, Yus M, Tetrahedron., 61, 11771 (2005)
Alonso F, Beletskaya IP, Yus M, Tetrahedron., 64, 3047 (2008)
Prabakaran K, Khan FN, Jin JS, Tetrahedron Letters., 52, 2566 (2011)
Liu SF, Xiao JL, J. Mol. Catal. A-Chem., 270(1-2), 1 (2007)
Polshettiwar V, Molnar A, Tetrahedron., 63, 6949 (2007)
Carpita A, Ribecai A, Tetrahedron Letters., 50, 204 (2009)
Shao L, Ji W, Dong P, Zeng M, Qi C, Zhng XM, Applied Catalysis A-General., 413-414, 267 (2012)
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Anastas PT, Williamson TC (Eds.), Green Chemistry: Designing Chemistry for the Environment, American Chemical Society, Washington DC (1996)
Tundo P, Anastas PT (Eds.), Green Chemistry: Challenging Perspectives, Oxford University Press, New York (2000)
Rollet P, Kleist W, Dufaud V, Djakovitch L, J. Mol. Catal. A-Chem., 241(1-2), 39 (2005)
Kappe CO, Stadler A, Microwave in Organic and Medicina Chemistry, Wiely-VCH, Weinheim (2005)
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Gigure RJ, Bray TL, Duncan SM, Magetich G, Tetrahedron Letters., 27, 4945 (1986)
Loupy A, Perreus L, Liagre M, Burle K, Moneus M, Pure and Applied Chemistry., 73, 161 (2001)
Chen Y, Markina NA, Larock RC, Tetrahedron., 65, 8908 (2009)
Sajith AM, Muralidharan A, Tetrahedron Letters., 53, 5206 (2012)
Huang H, Liu H, Jiang H, Chen K, Journal of Organic Chemistry., 73, 6037 (2008)
Tanaka K, Solvent-free Organic Synthesis, Wiely-VCH, Weinheim (2003)
Kabalka GW, Wang L, Pagni RM, Tetrahedron., 57, 8017 (2001)
Sonogashira K, Tohda Y, Tetrahedron Letters., 16, 4467 (1975)
Sonogashira K, in: Trost BM (Ed.), Comprehensive Organic Synthesis, vol. 3, Pergamon Press, Oxford, 521 (1999)
Chinchilla R, Najera C, Chemical Reviews., 107, 107 (2007)
Heravi MM, Sadjadi S, Tetrahedron., 65, 7761 (2009)
Lin JC, Kim JH, Kellar JA, Hersam MC, Nguyen ST, Bedzyk MJ, Langmuir, 26(6), 3771 (2010)
liang Y, Xie YX, Li JH, Journal of Organic Chemistry., 71, 379 (2006)
Urgaonkar S, Verkade JG, Journal of Organic Chemistry., 69, 5752 (2004)
Bhattacharya S, Sengupta S, Tetrahedron Letters., 45, 8733 (2004)
Erdelyl M, Gogoll A, Journal of Organic Chemistry., 66, 4165 (2001)
Erdelyl M, Gogoll A, Journal of Organic Chemistry., 68, 6431 (2003)
Awuah E, Capretta A, Organic Letters., 11, 3210 (2009)
Chang W, Shin J, Oh YH, Ahn BJ, J. Ind. Eng. Chem., 14(4), 423 (2008)
Chang W, Chae GH, Jang SR, Shin J, Ahn BJ, J. Ind. Eng. Chem., 18(2), 581 (2012)
Sotiriou-Leventis C, Wang X, Mulik S, Thangavel A, Leventis N, Synthetic Communications., 38, 2285 (2008)
Hosseinzadeh R, Mohadjerani M, Tavakoli R, Alikarami M, Synthetic Communications., 40, 282 (2010)
Unpublished results.
Soheili P, Albaneze-Walker J, Murry J, Dormer PG, Hughes DL, Organic Letters., 5, 4191 (2003)
Djakovitch L, Rollet P, Tetrahedron Letters., 45, 1367 (2004)

[Referenced By]

[1] Diederich F, Stang PJ (Eds.), Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim (1998)

[2] de Meijere A, Diederich F (Eds.), Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim (2004)

[3] Polshettiwar V, Len C, Fihri A, Coordination Chemistry Reviews., 253, 2599 (2009)

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

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

[6] Prabakaran K, Khan FN, Jin JS, Tetrahedron Letters., 52, 2566 (2011)

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

[8] Polshettiwar V, Molnar A, Tetrahedron., 63, 6949 (2007)

[9] Carpita A, Ribecai A, Tetrahedron Letters., 50, 204 (2009)

[10] Shao L, Ji W, Dong P, Zeng M, Qi C, Zhng XM, Applied Catalysis A-General., 413-414, 267 (2012)

[11] Domenech B, Munoz M, Muraviev DN, Macanas J, Catalysis Today. (2012)

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

[13] Anastas PT, Williamson TC (Eds.), Green Chemistry: Designing Chemistry for the Environment, American Chemical Society, Washington DC (1996)

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

[15] Rollet P, Kleist W, Dufaud V, Djakovitch L, J. Mol. Catal. A-Chem., 241(1-2), 39 (2005)

[16] Kappe CO, Stadler A, Microwave in Organic and Medicina Chemistry, Wiely-VCH, Weinheim (2005)

[17] Gedye RN, Smith FE, Westaway K, Ali H, Baldisera L, Laberge L, Rousell J, Tetrahedron Letters., 27, 279 (1986)

[18] Gigure RJ, Bray TL, Duncan SM, Magetich G, Tetrahedron Letters., 27, 4945 (1986)

[19] Loupy A, Perreus L, Liagre M, Burle K, Moneus M, Pure and Applied Chemistry., 73, 161 (2001)

[20] Chen Y, Markina NA, Larock RC, Tetrahedron., 65, 8908 (2009)

[21] Sajith AM, Muralidharan A, Tetrahedron Letters., 53, 5206 (2012)

[22] Huang H, Liu H, Jiang H, Chen K, Journal of Organic Chemistry., 73, 6037 (2008)

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

[24] Kabalka GW, Wang L, Pagni RM, Tetrahedron., 57, 8017 (2001)

[25] Sonogashira K, Tohda Y, Tetrahedron Letters., 16, 4467 (1975)

[26] Sonogashira K, in: Trost BM (Ed.), Comprehensive Organic Synthesis, vol. 3, Pergamon Press, Oxford, 521 (1999)

[27] Chinchilla R, Najera C, Chemical Reviews., 107, 107 (2007)

[28] Heravi MM, Sadjadi S, Tetrahedron., 65, 7761 (2009)

[29] Lin JC, Kim JH, Kellar JA, Hersam MC, Nguyen ST, Bedzyk MJ, Langmuir, 26(6), 3771 (2010)

[30] liang Y, Xie YX, Li JH, Journal of Organic Chemistry., 71, 379 (2006)

[31] Urgaonkar S, Verkade JG, Journal of Organic Chemistry., 69, 5752 (2004)

[32] Bhattacharya S, Sengupta S, Tetrahedron Letters., 45, 8733 (2004)

[33] Erdelyl M, Gogoll A, Journal of Organic Chemistry., 66, 4165 (2001)

[34] Erdelyl M, Gogoll A, Journal of Organic Chemistry., 68, 6431 (2003)

[35] Awuah E, Capretta A, Organic Letters., 11, 3210 (2009)

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

[37] Chang W, Chae GH, Jang SR, Shin J, Ahn BJ, J. Ind. Eng. Chem., 18(2), 581 (2012)

[38] Sotiriou-Leventis C, Wang X, Mulik S, Thangavel A, Leventis N, Synthetic Communications., 38, 2285 (2008)

[39] Hosseinzadeh R, Mohadjerani M, Tavakoli R, Alikarami M, Synthetic Communications., 40, 282 (2010)

[40] Unpublished results.

[41] Soheili P, Albaneze-Walker J, Murry J, Dormer PG, Hughes DL, Organic Letters., 5, 4191 (2003)

[42] Djakovitch L, Rollet P, Tetrahedron Letters., 45, 1367 (2004)