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5
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0038788894
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For alternative approaches not employing carboxylic acids, see: a
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For alternative approaches not employing carboxylic acids, see: a) N. Shangguan, S. Katukojvala, R. Greenberg, L. J. Williams, J. Am. Chem. Soc. 2003, 125, 7754-7755;
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c) N. Carrillo, E. A. Davalos, J. A. Russak, J. W. J. Bode, J. Am. Chem. Soc. 2006, 128, 1452-1453;
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34547896611
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d) C. Gunanathan, Y. Ben-David, D. Milstein, Science 2007, 317, 790-792;
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Gunanathan, C.1
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0001094491
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K. Ishihara, S. Ohara, H. Yamamoto, J. Org. Chem. 1996, 61, 4196-4197.
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Ishihara, K.1
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Maki, T.1
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33744790869
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K. Arnold, B. Davies, R. L. Giles, C. Grojean, G. E. Smith, A. Whiting, Adv. Synth. Catal. 2006, 348, 813-820.
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15
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0001659674
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Molecular sieves were shown to catalyze amidations at very high temperatures: J. Cossy, C. Pale-Grosdemange, Tetrahedron Lett. 1989, 30, 2771-2774. No such effect was observed under our reaction conditions.
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Molecular sieves were shown to catalyze amidations at very high temperatures: J. Cossy, C. Pale-Grosdemange, Tetrahedron Lett. 1989, 30, 2771-2774. No such effect was observed under our reaction conditions.
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16
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33751568118
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Catalyst 2 was synthesized based on a procedure by Scott and co-workers: H. A. Wegner, H. Reisch, K. Rauch, A. Demeter, K. A. Zachariasse, A. de Meijere, L. T. Scott, J. Org. Chem. 2006, 71, 9080-9087. See detailed procedure in Supporting Information.
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Catalyst 2 was synthesized based on a procedure by Scott and co-workers: H. A. Wegner, H. Reisch, K. Rauch, A. Demeter, K. A. Zachariasse, A. de Meijere, L. T. Scott, J. Org. Chem. 2006, 71, 9080-9087. See detailed procedure in Supporting Information.
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17
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85027844968
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P. Tang, H. Krause, A. Fürstner, Org. Synth. 2005, 81, 262-267.
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37049032619
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R. K. Mylavarapu, G. C. M. K. Kondaiah, N. Kolla, R. Veeramalla, P. Koilkonda, A. Bhattacharya, R. Bandichhor, Org. Process Res. Dev. 2007, 11, 1065-1068.
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19
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21
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0036589523
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Yuchun, X.1
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23
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53549130137
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The use of previously reported conditions (toluene, heating at reflux)[7] led to greater than 30% racemization
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[7] led to greater than 30% racemization.
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24
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53549126509
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[10] Further, we observed no formation of acetic anhydride when acetic acid and 2 are mixed alone under the same amidation conditions as in Table 1. Moreover, in the same conditions, butyric anhydride reacted efficiently with N-methylbenzylamine, a substrate that failed by direct amidation catalyzed by 2.
-
[10] Further, we observed no formation of acetic anhydride when acetic acid and 2 are mixed alone under the same amidation conditions as in Table 1. Moreover, in the same conditions, butyric anhydride reacted efficiently with N-methylbenzylamine, a substrate that failed by direct amidation catalyzed by 2.
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26
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53549123148
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2 8.8) and thus cannot explain its exceptional catalytic activity.
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2 8.8) and thus cannot explain its exceptional catalytic activity.
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27
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38349178582
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A. Erkkilä, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416-5470.
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28
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33947450628
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For example, the Diels-Alder reactions between acrylic acid and cyclopentadiene and furan require, respectively, one hour at 165°C and 75 days at 35°C to achieve reasonable yields of products: a F. X. Werber, J. E. Jansen, T. L. Gresham, J. Am. Chem. Soc. 1952, 74, 532-535;
-
For example, the Diels-Alder reactions between acrylic acid and cyclopentadiene and furan require, respectively, one hour at 165°C and 75 days at 35°C to achieve reasonable yields of products: a) F. X. Werber, J. E. Jansen, T. L. Gresham, J. Am. Chem. Soc. 1952, 74, 532-535;
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30
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53549104555
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Phenylboronic acid gave only 25% yield under the same conditions
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Phenylboronic acid gave only 25% yield under the same conditions.
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31
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53549132978
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Contrary to amidations where attack of the amine regenerates the catalyst (Scheme 3A), a small amount of water (from condensation of the acid and the catalyst) is required to regenerate the catalyst from the cycloadduct.
-
Contrary to amidations where attack of the amine regenerates the catalyst (Scheme 3A), a small amount of water (from condensation of the acid and the catalyst) is required to regenerate the catalyst from the cycloadduct.
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32
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0000224603
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K. Furuta, Y. Miza, K. Iwanaga, H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 6254-6255.
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Hyun Ryu, D.1
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34
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34347335758
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For an excellent essay on cascade catalysis, see
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For an excellent essay on cascade catalysis, see: A. M. Walji, D.W. C. MacMillan, Synlett 2007, 1477-1489.
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(2007)
Synlett
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Walji, A.M.1
MacMillan, D.W.C.2
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