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2012 | 1 | 10-33
Article title

Pd-anchored functionalized mesoporous materials as robust
and recyclable heterogeneous catalysts for a series of C-C
bond forming reactions

Content
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EN
Abstracts
EN
Pd-catalyzed C-C bond forming reactions have attracted huge interest
not only among the synthetic organic chemists but researchers of various
disciplines for over two decades because a large panorama of value added
organic target molecules can be designed employing this synthesis protocol.
Richard F. Heck, Ei-ichi Negishi and Akira Suzuki have been awarded the
Nobel Prize in Chemistry 2010 for their pioneering works on these palladiumcatalyzed
cross-coupling reactions in organic synthesis. More greener and
eco-friendly synthetic conditions together with the recyclability of the Pdcatalyst
have been continuously hunted over the years. It is essential to know
the different steps and mechanism involved in these C-C coupling reactions
together with the active Pd-sites present at the catalytic surfaces. In this
review we have focused on discussing various protocols involved in the C-C
coupling reactions and gradual developments in Pd-grafted functionalized
mesoporous materials. Recyclability and sustainability of the catalyst along
with their surface modification strategies have been discussed. Catalytic
efficiency of these functionalized mesoporous materials largely depends on
strong binding of the Pd-sites with the support matrix. Thus, discussion on
different types of supports has also been made.
Publisher

Year
Volume
1
Pages
10-33
Physical description
Dates
accepted
03 - 04 - 2013
online
23 - 04 - 2013
received
30 - 11 - 2012
Contributors
author
  • Department of Materials Science,
    Indian Association for the Cultivation of Science,
    Jadavpur 700 032, India
author
  • Department of Materials Science,
    Indian Association for the Cultivation of Science,
    Jadavpur 700 032, India
author
  • Department of Materials Science,
    Indian Association for the Cultivation of Science,
    Jadavpur 700 032, India
author
  • Department of Materials Science,
    Indian Association for the Cultivation of Science,
    Jadavpur 700 032, India
References
  • J. N. Armor, Catal. Today, 163, 3 (2011).
  • J. Berzelius, Jahres-Bericht über die Fortschritte derPhysichen Wissenschaften, H. Laupp, Tübingen (1836).
  • F. Zaera, Chem Soc Rev., 42, 2746 (2013).[PubMed]
  • Y. Nishihata, J. Mizuki, T. Akao, H. Tanaka, M. Uenishi, M.Kimura, T. Okamoto, N. Hamada, Nature, 418, 164 (2002).
  • T. Mallat, E. Orglmeister, A. Baiker, Chem. Rev., 107, 4863(2007).
  • C. V. Reddy, J. V. Kingston, J. G. Verkade, J. Org. Chem., 73,3047 (2008).
  • S. Loua, G. C. Fu, Adv. Synth. Catal., 352, 2081 (2010).
  • A. Ohtaka, Y. Tamaki, Y. Igawa, K. Egami, O. Shimomura, R.Nomura, Tetrahedron 66, 5642 (2010).
  • B. Karimi, D. Enders, Org. Lett., 8, 1237 (2006).
  • R. Dey, B. Sreedhar, B. C. Ranu, Tetrahedron 66, 2301(2010).
  • A. F. Littke, G. C. Fu, J. Am. Chem. Soc., 123, 6989 (2001).
  • H. Azoui, K. Baczko, S. Cassel, C. Larpent, Green Chem.,10, 1197 (2008).
  • D. Saha, K. Chattopadhyay, B. C. Ranu, Tetrahedron Lett.,50, 1003 (2009).
  • N. J. Whitcombe, K. K. Hii, S. E. Gibson, Tetrahedron 57,7449 (2001).
  • A. F. Littke, G. C. Fu, Angew. Chem., Int. Ed., 41, 4176 (2002).
  • R. B. Bedford, Chem. Commun., 1787 (2003).
  • C. S. Consorti, M. L. Zanini, S. Leal, G. Ebeling, J. Dupont,Org. Lett., 5, 983 (2003).
  • A. J. Carmichael, M. J. Earle, J. D. Holbrey, P. B. McCormac,K. R. Seddon, Org. Lett., 1, 997 (1999).
  • K. S. A. Vallin, P. Emilsson, M. Larhed, A. Hallberg, J. Org.Chem., 67, 6243 (2002).
  • S. B. Park, H. Alper, Org. Lett., 5, 3209 (2003).
  • C. J. Welch, J. Albaneze-Walker, W. R. Leonard, M. Biba,J. DaSilva, D. Henderson, B. Laing, D. J. Mathre, S. Spencer, X. Bu, T. Wang, Org. Process Res. Dev., 9, 198(2005).
  • C. E. Garrett, K. Prasad, Adv. Synth. Catal., 346, 889 (2004).
  • J. G. de Vries, Can. J. Chem., 79, 1086 (2001).
  • H.-U. Blaser, A. Indolese, A. Schnyder, H. Steiner, M. Studer,J. Mol. Catal. A: Chem., 3, 173 (2001).
  • C. E. Tucker, J. G. De Vries, Top. Catal., 19, 111 (2002).
  • B. M. Bhanage, M. Arai, Catal. Rev., 43, 315 (2001).
  • F. Zhao, B. M. Bhanage, M. Shirai, M. Arai, Chem. Eur. J., 6,843 (2000).
  • H. Hagiwara, Y. Shimizu, T. Hoshi, T. Suzuki, M. Ando, K.Ohkubo, C. Yokoyama, Tetrahedron Lett., 42, 4349 (2001).
  • A. Biffis, M. Zecca, M. Basato, J. Mol. Catal. A: Chem., 173,249 (2001).
  • C. P. Mehnert, D. W. Weaver, J. Y. Ying, J. Am. Chem. Soc.,120, 12289 (1998).
  • L. Djakovitch, K. Koehler, J. Am. Chem. Soc., 123, 5990(2001).
  • M. K. Bhunia, S. K. Das, P. Pachfule, R. Banerjee, A.Bhaumik, Dalton Trans., 41, 1304 (2012).[PubMed]
  • A. Biffis, M. Zecca, M. Basato, Eur. J. Inorg. Chem., 1131 (2001).
  • M. Wagner, K. Ko¨hler, L. Djakovitch, S. Weinkauf, V. Hagen,M. Muhler, Top. Catal., 13, 319 (2000).
  • K. Ko¨hler, M. Wagner, L. Djakovitch, Catal. Today 66, 105(2001).
  • R. K. Ramchandani, B. S. Uphade, M. P. Vinod, R. D.Wakharkar, V. R. Choudhary, A. Sudalai, Chem. Commun.,2071 (1997).
  • R. S. Varma, K. P. Naicker, P. J. Liesen, Tetrahedron Lett., 40,2075 (1999).
  • J. Li, A. W. H. Mau, C. R. Strauss, Chem. Commun., 1275(1997).
  • S. Ogasawara, S. Kato, J. Am. Chem. Soc., 132, 4608(2010).
  • A. Biffis, M. Zecca, M. Basato, J. Mol. Catal. A: Chem., 173,249 (2001).
  • J. H. Clark, J. Macquarrie, E. B. Mubofu, Green Chem., 2, 53(2000).
  • J. Zhou, R. Zhou, L. Mo, S. Zhao, X. Zheng, J. Mol. Catal. A:Chem., 178, 289 (2002).
  • K. Sarkar, M. Nandi, M. Islam, M. Mubarak, A. Bhaumik,Appl. Catal. A.: Gen., 352, 81 (2009).
  • M. Dams, L. Drijkoningen, B. Pauwels, G. Van Tendeloo, D.E. DeVos, P. A. Jacobs, J. Catal., 209, 225 (2002).
  • A. Corma, H. Garcia, A. Leyva, A. Primo, Appl. Catal., A:Gen., 247, 41 (2003).
  • A. Corma, H. Garcia, A. Leyva, A. Primo, Appl. Catal., A:Gen., 257, 77 (2004).
  • L. Djakovitch, M. Wagner, C. G. Hartung, M. Beller, K.Koehler, J. Mol. Catal. A: Chem., 219, 121 (2004).
  • R. G. Heidenreich, J. G. E. Krauter, J. Pietsch, K. Ko¨hler, J.Mol. Catal. A: Chem., 182, 499 (2002).
  • D. S. Ennis, J. Mcmanus, W. Wood-Kaczmar, J. Richardson,G. E. Smith, A. Carstais, Org. Process Res. Dev., 3, 248(1999).
  • L. Yin, J. Liebscher, Chem. Rev., 107, 133 (2007).
  • I. Yuranov, P. Moeckli, E. Suvorova, P. Buffat, L. Kiwi- Minsker,A. Renken, J. Mol. Catal. A: Chem., 192, 239 (2003).
  • J. Mondal, A. Modak, A. Dutta, A. Bhaumik, Dalton Trans. 40,5228 (2011).[PubMed]
  • J. Mondal, T. Sen, A. Bhaumik, Dalton Trans. 41, 6173(2012).[PubMed]
  • A. Bhaumik, T. Tatsumi, J. Catal., 189, 39 (2000).
  • S. Inagaki, S. Guan, Y. Fukushima, T. Ohsuna, O. Terasaki, J.Am. Chem. Soc., 121, 9611 (1999).
  • A. Modak, J. Mondal, V. K. Aswal, A. Bhaumik, J. Mater.Chem., 20, 8099 (2010).
  • K. Dhara, K. Sarkar, D. Srimani, S. K. Saha, P. Chattopadhyaye,A. Bhaumik, Dalton Trans., 39, 6395 (2010).[PubMed]
  • S. Mandal, D. Roy, R. V. Chaudhari, M. Sastry, Chem. Mater.,16, 3714 (2004).
  • C. Gonzalez-Arellano, A. Corma, M. Iglesias, F. Sanchez,Adv. Synth. Catal., 346, 1758 (2004).
  • M. Nandi, M. Islam, P. Mondal, A. Bhaumik, Eur. J. Inorg.Chem. 221 (2011).
  • P. Selvam, S. K. Mohapatra, S. U. Sonavane, R. V. Jayaram,Appl. Catal., B 49, 251 (2004).
  • Y. Jiang, Q. Gao, J. Am. Chem. Soc., 128, 716 (2006).
  • S. B. Waghmode, S. G. Wagholikar, S. Sivasanker, Bull.Chem. Soc. Jpn., 76, 1989 (2003).
  • R. Narayanan, C. Tabor, M. A. El-Sayed, Top. Catal., 48, 60 (2008).
  • K. R. McCrea, J. S. Parker, G. A. Somorjai, J. Phys. Chem.B, 106, 10854 (2002).
  • S.-W. Kim, M. Kim, W. Y. Lee, T. Hyeon, J. Am. Chem. Soc.,124, 7642 (2002).
  • R. Ul Islam, M. J. Witcomb, M. S. Scurrell, E. V. Lingen, W. V.Otterloc, K. Mallick, Catal. Sci. Technol., 1, 308 (2011).
  • R. Gangopadhyay, A. De, Chem. Mater., 12, 608 (2000).
  • J. Mondal, A. Modak, M. Nandi, H. Uyama, A. Bhaumik, RSCAdv., 2, 11306 (2012).
  • C. F-Martin, M. Birot, H. Deleuze, A. Desforges, R. Backov,React. Funct. Polymer, 67, 1072 (2007).
  • N. Toshima, Y. Wang, Adv. Mater., 6, 245 (1994).
  • Y. Mizukoshi, K. Okitsu, Y. Maeda, T. A. Yamamoto, R.Oshima, Y. Nagata, J. Phys. Chem. B, 101, 7033 (1997).
  • N. Miyaura, A. Suzuki, Chem. Rev., 95, 2457 (1995).
  • R. F. Heck, J. P. Nolly, J. Org. Chem., 37, 2320 (1972).
  • Y. Uozumi, Top. Curr. Chem., 242, 77 (2004).
  • K.-i. Shimizu, S. Koizumi, T. Hatamachi, H. Yoshida, S.Komai, T. Kodama, Y. Kitayama, J. Catal., 228, 141 (2004).
  • K. Yu, W. Sommer, J. M. Richardson, M. Weck, C. W. Jones,Adv. Synth. Catal., 347, 161 (2005).
  • J. H. Clark, J. Macquarrie, E. B. Mubofu, Green Chem., 2, 53(2000).
  • J. Horniakova, T. Raja, Y. Kubota, Y. Sugi, J. Mol. Catal. A:Chem., 217, 73 (2004).
  • Y. S. Choi, E. G. Moschetta, J. T. Miller, M. Fasulo, M. J.McMurdo, R. M. Rioux, T. Don Tilley, ACS Catal., 1, 1166(2011).
  • J. Pecher, S. Mecking, Chem. Rev., 110, 6260 (2010).[PubMed]
  • J.-X. Jiang, C. Wang, A. Laybourn, T. Hasell, R. Clowes, Y.Z. Khimyak, J. Xiao, S. J. Higgins, D. J. Adams, A. I. Cooper,Angew. Chem., Int. Ed., 50, 1072 (2011).
  • C. E. Chan-Thaw, A. Villa, P. Katehomol, D. Su, A. Thomas,L. Prati, Nano Lett., 10, 537 (2010).
  • T. Hasell, C. D. Wood, R. Clowes, J. T. A. Jones, Y. Z.Khimyak, D. J. Adams, A. I. Cooper, Chem. Mater., 22, 557(2010).
  • P. Zhang, Z. Weng, J. Guo, C. Wang, Chem. Mater., 23, 5243(2011).
  • A. Desforges, R. Backov, O. M-Monval, Adv. Funct. Mater.,15, 1689 (2005).
  • A. Desforges , H. Deleuze, O. M-Monval, R. Backov, Ind.Eng. Chem. Res., 44 (23), 8521 (2005).
  • D. Chandra, T. Yokoi, T. Tatsumi, A. Bhaumik, Chem. Mater.,19, 5347 (2007).
  • D. Chandra, A. Bhaumik, J. Mater. Chem., 19, 1901 (2009).
  • J. Mondal, A. Modak, A. Bhaumik, J. Mol. Catal. A: Chem.,350, 40 (2011).
  • A. Modak, J. Mondal, M. Sasidharan, A. Bhaumik, GreenChem., 13, 1317 (2011).
  • K. Mukhopadhyay, B. R. Sarkar, R. V. Chaudhari, J. Am.Chem. Soc., 124, 9692 (2002).
  • L. Li, J-L. Shi, J-N. Yan, Chem. Commun., 1990 (2004).
  • F. Wang, C. Li, L-D. Sun, C-H. Xu, J. Wang, J. C. Yu, C-H.Yan, Angew. Chem., Int. Ed., 51, 4872 (2012).
  • L. Wang, D. Dehe, T. Philippi, A. Seifert, S. Ernst, Z. Zhou, M.Hartmann, R. N. K. Taylor, A. P. Singh, M. Jiab, W. R. Thiel,Catal. Sci. Technol., 2, 1188 (2012).
  • H. Li, W. Chai, F. Zhang, J. Chen, Green Chem., 9, 1223(2007).
  • J. Schmidt, J. Weber, J. D. Epping, M. Antonietti, A. Thomas,Adv. Mater., 21, 702 (2009).
  • J.-X. Jiang, F. Su, A. Trewin, C. D. Wood, N. L. Campbell,H. Niu, C. Dickinson, A. Y. Ganin, M. J. Rosseinsky, Y. Z.Khimyak, A. I. Cooper, Angew. Chem., Int. Ed., 46, 8547(2007).
  • M. Chatterjee, T. Ishizaka, T. Suzuki, A. Suzuki, H. Kawanami,Green Chem., 14, 3415-3422 (2012).
  • B. Karimi, A. Zamani, Org. Biomol. Chem., 10, 4531 (2012).
  • C. M. Crudden, M. Sateesh, R. Lewis, J. Am. Chem. Soc.,127, 10045 (2005).
  • X. Xu, Y. Li, Y. Gong, P. Zhang, H. Li, Y. Wang, J. Am. Chem.Soc., 134, 16987 (2012).
  • S. V. Vasilyeva, M. A. Vorotyntsev, I. Bezverkhyy, E.Lesniewska, O. Heintz, R. Chassagnon, J. Phys. Chem. C,112, 19878 (2008).
  • S. Santra, K. Dhara, P. Ranjan, P. Bera, J. Dash, S. K. Mandal,Green Chem., 13, 3238 (2011).
  • N. Brun, P. Hesemann, G. Laurent, C. Sanchez, M. Birot, H.Deleuze, R. Backov, New J. Chem., 37, 157-168 (2013).
  • N. Miyaura, K. Yamada, A. Suzuki, Tetrahedron Lett., 20,3437 (1979).
  • N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun., 11, 513(1981).
  • A. Molnár, Chem. Rev., 111, 2251 (2011).[PubMed]
  • V. Polshettiwar, A. Decottignies, C. Len, A. Fihri,ChemSusChem, 3, 502 (2010).[PubMed]
  • E. B. Mubofu, J. H. Clark, D. J. Macquarrie, Green Chem., 3,23 (2001).
  • S. Paul, J. H. Clark, Green Chem., 5, 635 (2003).
  • R. B. Bedford, C. S.J. Cazin, M. B. Hursthouse, M. E. Light,K. J. Pike, S. Wimperis, J. Organomet. Chem., 633, 173(2001).
  • C. Baleiza˜o, A. Corma, H. Garcı´a, A. Leyva, Chem.Commun., 606 (2003).
  • A. Fihri, D. Cha, M. Bouhrara, N. Almana, V. Polshettiwar,ChemSusChem., 5, 85 (2012).[PubMed]
  • A. Fihri, M. Bouhrara, B. Nekoueishahraki, J-M. Basset, V.Polshettiwar, Chem. Soc. Rev., 40, 5181 (2011).[PubMed]
  • T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn., 44, 581(1971).
  • M. Beller, A. Tafesh, W. A. Herrmann, German Patent DE19503/119 (1996).
  • S. Durgadas, V. K. Chatare, K. Mukkanti, S. Pal, Appl.Organomet. Chem., 24, 680 (2010).
  • A. Papp, G. Galba´cs, Ä. Molna´r, Tetrahedron Lett., 46, 7725(2005).
  • C. P. Mehnert, J. Y. Ying, Chem. Commun., 2215 (1997).
  • M. Z. Cai, C. S. Song, X. Huang, Synthesis, 521 (1997).
  • M. Cai, Y. Huang, H. Zhao, C. Song, React. Funct. Polym.,59, 81 (2004).
  • M. Cai, G. Liu, J. Zhou, J. Mol. Catal. A: Chem., 227, 107(2005).
  • M. Lagasi, P. Moggi, J. Mol. Catal. A: Chem., 61, 182 (2002).
  • B. Karimi, D. Enders, Org. Lett., 8, 1237 (2006).
  • N. Kim, M. S. Kwon, C. M. Park, J. Park, Tetrahedron Lett.,45, 7057 (2004).
  • L. Li, L. Zhang, J. Shi, J. Yan, J. Liang, Appl. Catal., A: Gen.,283, 85 (2005).
  • B. M. Choudary, N. S. Chowdari, K. Jyothi, N. S. Kumar, M.L. Kantam, Chem. Commun., 586 (2002).
  • V. Polshettiwar, A. Molnar, Tetrahedron, 63, 6949 (2007).
  • G. T. Crisp, Chem. Soc. Rev., 27, 427 (1998).
  • B. L. Shaw, New J. Chem., 77 (1998).
  • A. Sundermann, O. Uzan, J. M. L. Martin, Chem. Eur. J., 7,1703 (2001).
  • M. T. Reetz, J. G. de Vries, Chem. Commun., 1559 (2004).
  • M. Lamblin, L. Nassar-Hardy, J-C. Hierso, E. Fouquet, F-X.Felpinb, Adv. Synth. Catal., 352, 33 (2010).
  • J. Rebeck, F. Gavina, J. Am. Chem. Soc., 96, 7112 (1974).
  • J. P. Collmann, K. M. Kosydar, M. Bressan, W. Lamanna, T.Garrett, J. Am. Chem. Soc., 106, 2569 (1984).
  • I. W. Davies, L. Matty, D. L. Hughes, P. J. Reider, J. Am.Chem. Soc., 123, 10139 (2001).
  • M. Perez-Lorenzo, J. Phys. Chem. Lett., 3, 167 (2012).
  • M. Choi, H. S. Cho, R. Srivastava, C. Venkatesan, D. H. Choi,R. Ryoo, Nature Mater. 5, 718 (2006).
  • M. Fujiwara, A. Sakamoto, K. Shiokawa, A. K. Patra, A.Bhaumik, Microporous Mesoporous Mater. 142, 381 (2011).
  • R. Ravetti-Duran, J. L. Blin, M. J. Stébé, C. Castel, A. Pasc,J. Mater. Chem., 22, 21540 (2012).
  • S. Ungureanu, H. Deleuze, C. Sanchez, M. I. Popa, R.Backov, Chem. Mater., 20, 6494 (2008).
  • S. Ungureanu, H. Deleuze, O. Babot, M.-F. Achard, C.Sanchez, M.I. Popa, R. Backov, Appl. Catal. A.: Gen., 390,51 (2010).
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_recat-2013-0001
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