PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
2012 | 1 | 10-33
Tytuł artykułu

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

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
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.
Wydawca
Rocznik
Tom
1
Strony
10-33
Opis fizyczny
Daty
otrzymano
2012-11-30
zaakceptowano
2013-04-03
online
2013-04-23
Twórcy
autor
  • Department of Materials Science,
    Indian Association for the Cultivation of Science,
    Jadavpur 700 032, India
autor
  • Department of Materials Science,
    Indian Association for the Cultivation of Science,
    Jadavpur 700 032, India
  • Department of Materials Science,
    Indian Association for the Cultivation of Science,
    Jadavpur 700 032, India
autor
  • Department of Materials Science,
    Indian Association for the Cultivation of Science,
    Jadavpur 700 032, India
Bibliografia
  • 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).
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_recat-2013-0001
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.