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For an excellent recent review see: E. L. Margelefsky, R. K. Zeidan, M. E. Davis, Chem. Soc. Rev. 2008, 37, 1118-1126.
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For reviews on mesoporous materials and application to catalysis see: a
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For reviews on mesoporous materials and application to catalysis see: a) A. Corma, Chem. Rev. 1997, 97, 2373-2419;
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For description of the co-condensation method see: a
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For description of the co-condensation method see: a) S. Huh, J. W. Wiench, J.-C. Yoo, M. Pruski, V. S.-Y. Lin, Chem. Mater. 2003, 15, 4247-4256;
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Chem. Mater
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Huh, S.1
Wiench, J.W.2
Yoo, J.-C.3
Pruski, M.4
Lin, V.S.-Y.5
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b) S. Huh, J. W. Wiench, B. J. Trewyn, M. Pruski, V. S.-Y. Lin, Chem. Commun. 2003, 2364-2365;
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Lin, V.S.-Y.5
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c) R. Kumar, H.-T. Chen, J. L. V. Escoto, V. S.-Y. Lin, M. Pruski, Chem. Mater. 2006, 18, 4319-4327.
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Pruski, M.5
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12
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18644365075
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For a comparison between co-condensation and post-synthetic grafting methods see: d
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For a comparison between co-condensation and post-synthetic grafting methods see: d) M. H. Lim, A. Stein, Chem. Mater. 1999, 11, 3285-3295;
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e) P. D. Vaz, C. D. Nunes, M. Vasconcellos-Dias, M. M. Nolasco, P. J. A. Ribeiro-Claro, M. J. Calhorda, Chem. Eur. J. 2007, 13, 7874-7882.
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Nolasco, M.M.4
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Angew. Chem. Int. Ed
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For reviews on supported organic catalysts see: a
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For reviews on supported organic catalysts see: a) A. Puglisi, F. Cozzi, M. Benaglia, Chem. Rev. 2003, 103, 3401-3430;
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Puglisi, A.1
Cozzi, F.2
Benaglia, M.3
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20
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33645421754
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Reactions in which the silanol residues of the silica surface participate to the catalytic activity of a mono-functional catalyst supported on the same surface are not considered as occurring under co-operative catalysis. For examples, see: a J. D. Bass, A. Soloyvov, A. J. Pascall, A. Katz, J. Am. Chem. Soc. 2006, 128, 3737-3747;
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Reactions in which the silanol residues of the silica surface participate to the catalytic activity of a mono-functional catalyst supported on the same surface are not considered as occurring under co-operative catalysis. For examples, see: a) J. D. Bass, A. Soloyvov, A. J. Pascall, A. Katz, J. Am. Chem. Soc. 2006, 128, 3737-3747;
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23
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Angew. Chem. Int. Ed
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See also: d
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See also: d) K. Motokura, M. Tomita, M. Tada, Y. Iwasawa, Chem. Eur. J. 2008, 14, 4017-4027.
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Chem. Eur. J
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Motokura, K.1
Tomita, M.2
Tada, M.3
Iwasawa, Y.4
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25
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0942265481
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By the same token, reactions in which the catalytic activity of a mono-functional supported catalyst is tuned by the presence of a neighboring organic residue affecting the polarity around the catalytic sites but not involved in the catalytic cycle are also not considered examples of co-operative catalysis: e S. Huh, H. T. Chen, J. W. Wiench, M. Pruski, V. S.-Y. Lin, J. Am. Chem. Soc. 2004, 126, 1010-1011.
-
By the same token, reactions in which the catalytic activity of a mono-functional supported catalyst is tuned by the presence of a neighboring organic residue affecting the polarity around the catalytic sites but not involved in the catalytic cycle are also not considered examples of co-operative catalysis: e) S. Huh, H. T. Chen, J. W. Wiench, M. Pruski, V. S.-Y. Lin, J. Am. Chem. Soc. 2004, 126, 1010-1011.
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S. Huh, H.-T. Chen, J. W. Wiench, M. Pruski, V. S.-Y. Lin, Angew. Chem. 2005, 117, 1860-1864;
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Huh, S.1
Chen, H.-T.2
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Angew. Chem. Int. Ed. 2005, 44, 1826-1830.
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56449110527
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For a very recent contribution see also: K. Motokura, M. Tada, Y. Iwasawa Angew. Chem. Int. Ed. 2008, 47, 9230-9235.
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For a very recent contribution see also: K. Motokura, M. Tada, Y. Iwasawa Angew. Chem. Int. Ed. 2008, 47, 9230-9235.
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a) R. K. Zeidan, V. Dufaud, M. E. Davis, J. Catal. 2006, 239, 299-306;
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Zeidan, R.K.1
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Davis, M.E.3
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34250816631
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b) R. K. Zeidan, S.-J. Hwang, M. E. Davis, Angew. Chem. 2006, 118, 6480-6483;
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Angew. Chem
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Angew. Chem. Int. Ed. 2006, 45, 6332-6335;
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Angew. Chem. Int. Ed
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33
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35948978979
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For the synthesis and catalytic activity of a mesoporous siliceous material carrying a sulfonic acid and a thiol group tethered to the surface through a single chain see: E. L. Margelefsky, R. K. Zeidan, V. Dufaud, M. E. Davis, J. Am. Chem. Soc. 2007, 129, 13691-13697
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For the synthesis and catalytic activity of a mesoporous siliceous material carrying a sulfonic acid and a thiol group tethered to the surface through a single chain see: E. L. Margelefsky, R. K. Zeidan, V. Dufaud, M. E. Davis, J. Am. Chem. Soc. 2007, 129, 13691-13697.
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34
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a) T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672-12673.
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Okino, T.1
Hoashi, Y.2
Takemoto, Y.3
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35
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44349168328
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For a recent review on this and related reactions, see: b
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For a recent review on this and related reactions, see: b) S. J. Connon, Chem. Commun. 2008, 2499-2510.
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(2008)
Chem. Commun
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Connon, S.J.1
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36
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58549103015
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For recent examples of the use of non-supported bi-functional tertiary amine/thiourea catalysts see: c J. M. Andres, R. Manzano, R. Pedrosa, Chem. Eur. J. 2008, 14, 56116-55119;
-
For recent examples of the use of non-supported bi-functional tertiary amine/thiourea catalysts see: c) J. M. Andres, R. Manzano, R. Pedrosa, Chem. Eur. J. 2008, 14, 56116-55119;
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37
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44449113309
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d) L.-Q. Lu, Y.-J. Cao, X.-P. Liu, J. An, C.-J. Yao, Z.-H. Ming, W.-J. Xiao, J. Am. Chem. Soc. 2008, 130, 6946-6948;
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J. Am. Chem. Soc
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Lu, L.-Q.1
Cao, Y.-J.2
Liu, X.-P.3
An, J.4
Yao, C.-J.5
Ming, Z.-H.6
Xiao, W.-J.7
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44949230317
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e) S. E. Reisman, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 7198-7199.
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J. Am. Chem. Soc
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Reisman, S.E.1
Doyle, A.G.2
Jacobsen, E.N.3
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39
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48649106016
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For a review on hydrogen-bond mediated organocatalysis see
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For a review on hydrogen-bond mediated organocatalysis see: X. Yu, W. Wang, Chem. Asian J. 2008, 3, 516-532.
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Chem. Asian J
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Yu, X.1
Wang, W.2
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33748525817
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M. Longhi, V. Bertacche, C. L. Bianchi, L. Formaro, Chem. Mater. 2006, 18, 4130-4136.
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Longhi, M.1
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Formaro, L.4
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42
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58549114966
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These results together with recent findings in our laboratories indicated that FT-IR could be used as a routine method for the preliminary structural investigation of this type of materials. The use of this technique can be very convenient for checking the structural integrity of a recovered supported catalyst to be use in recycling experiments
-
These results together with recent findings in our laboratories indicated that FT-IR could be used as a routine method for the preliminary structural investigation of this type of materials. The use of this technique can be very convenient for checking the structural integrity of a recovered supported catalyst to be use in recycling experiments.
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43
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27144522622
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J. Wang, H. Li, W. Duan, L. Zu, W. Wang, Org. Lett. 2005, 7, 4713-4716.
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Wang, J.1
Li, H.2
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44
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33846648753
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It has been recently shown that a silica-supported sodium sulfonate can promote the conjugate addition of indoles to unsaturated ketones only in the presence of ionic liquids: Y. Gu, C. Ogawa, S. Kobayashi, Org. Lett. 2007, 9, 175-178
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It has been recently shown that a silica-supported sodium sulfonate can promote the conjugate addition of indoles to unsaturated ketones only in the presence of ionic liquids: Y. Gu, C. Ogawa, S. Kobayashi, Org. Lett. 2007, 9, 175-178.
-
-
-
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45
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58549095350
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-
In other words, this means that when catalyst 1 was used the catalyst loading was approximately 5 mol% each for the tertiary amine and the thiourea residues
-
In other words, this means that when catalyst 1 was used the catalyst loading was approximately 5 mol% each for the tertiary amine and the thiourea residues.
-
-
-
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46
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58549094410
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Neither the use of larger amount of extracting diethyl ether, nor the use of other solvents (dioxane, methanol, dichloromethane) both at room and at high temperature allowed the isolation of white materials
-
Neither the use of larger amount of extracting diethyl ether, nor the use of other solvents (dioxane, methanol, dichloromethane) both at room and at high temperature allowed the isolation of white materials.
-
-
-
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47
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58549105617
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After drying the supported catalyst at 150°C for 4 h under vacuum the material appeared to be not yellow anymore but a light grey powder.
-
After drying the supported catalyst at 150°C for 4 h under vacuum the material appeared to be not yellow anymore but a light grey powder.
-
-
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48
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58549099373
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The integrity of catalyst 1 was clearly demonstrated by TGA analysis that showed no traces of degradation of the supported catalyst until 200°C.
-
The integrity of catalyst 1 was clearly demonstrated by TGA analysis that showed no traces of degradation of the supported catalyst until 200°C.
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50
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0342445773
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E. P. Barrett, L. G. Joyner, P. Halenda, J. Am. Chem. Soc. 1951, 73, 373.
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