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0033607004
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Recent examples of transition metal-exchanged HT catalysts: B. Sels, D. De Vos, M. Buntinx, F. Pierard, A. Kirsch-De Mesmaeker, and P. Jacobs Nature 400 1999 855
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0003011263
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Base catalysis of HTs: M.L. Kantam, B.M. Choudary, C.V. Reddy, K.K. Rao, and F. Figueras Chem. Commun. 1998 1033
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0346116777
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For homogeneous catalytic α-alkylation of nitriles with primary alcohols, see: R. Grigg, T.R.B. Mitchell, S. Sutthivaiyakit, and N. Tongpenyai Tetrahedron Lett. 22 1981 4107
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Tongpenyai, N.4
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0037190865
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for α-alkylation of ketones with primary alcohols, see also: C.S. Cho, B.T. Kim, T.-J. Kim, and S.C. Shim Tetrahedron Lett. 43 2002 7987
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32744457670
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note
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For example, the reaction of ethyl cyanoacetate (1 ) with benzyl alcohol using the Ru/HT afforded undesirable benzyl cyanoacetate (base-catalyzed transesterification product) and the alkylation product was not formed.
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0037184451
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B.M. Choudary, S. Madhi, N.S. Chowdari, M.L. Kantam, and B. Sreedhar J. Am. Chem. Soc. 124 2002 14127
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Choudary, B.M.1
Madhi, S.2
Chowdari, N.S.3
Kantam, M.L.4
Sreedhar, B.5
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3042531840
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Recently, a Rh complex anchored on a silica matrix was reported for one-pot synthesis of ethyl 2-cyano-3-phenylpropanoate: F. Goettmann, D. Grosso, F. Mercier, F. Mathey, and C. Sanchez Chem. Commun. 2004 1240
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(2004)
Chem. Commun.
, pp. 1240
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Goettmann, F.1
Grosso, D.2
Mercier, F.3
Mathey, F.4
Sanchez, C.5
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32744454558
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note
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3, was obtained from TOMITA Pharmaceutical Co., Ltd.
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32744454811
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note
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The Pd/carbons were purchased from N.E. Chemcat Co. Ltd (0.5 wt %) and Wako Pure Chemical Ind., Ltd (5.0 wt %).
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32744467279
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note
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In a large-scale reaction, 1 (1.70 g, 15 mmol), 2 (1.59 g, 15 mmol), the Pd/HT (0.1 wt %, 0.60 g, Pd: 0.006 mmol), and toluene (20 mL) was used. After the aldol reaction (80°C, 3 h) and the hydrogenation (80°C, 20 h), the catalyst was filtered and GC analysis of the filtrate showed a 97% yield of 4. The filtrate was evaporated and the crude product was purified by distillation (180°C/5.0 mmHg) to afford pure product (2.9 g, 95% yield, TON = 2380).
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note
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2) using 1 with 2, corresponding alkylated product (4 ) was obtained, however, the yield was low (61%, after 1 h, 80°C) compared to that in the consecutive reaction and benzyl alcohol was formed as a byproduct.
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0020694416
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C.A. Bernhart, C. Condamine, H. Demarne, R. Roncucci, J.-P. Gagnol, P.J. Gautier, and M.A. Serre J. Med. Chem. 26 1983 451
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Bernhart, C.A.1
Condamine, C.2
Demarne, H.3
Roncucci, R.4
Gagnol, J.-P.5
Gautier, P.J.6
Serre, M.A.7
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