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  • 1 School of Science, The University of Tokyo Department of Chemistry Hongo, Bunkyo-ku Tokyo 113-0033 Japan
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Continuous-flow hydrogenation of aromatic nitro compounds was successfully performed by using polysilane-supported palladium catalysts to afford the corresponding amino compounds in high yields. Productivity was high, and a wide variety of nitro compounds were applicable under the continuous-flow conditions. It is noted that no leaching of palladium was observed by inductively coupled plasma analysis.

  • For selected reviews, see: (a) Puglisi, A.; Benaglia, M.; Chiroli, V. Green Chem. 2013, 15, 1790–1813; (b) McQuade, D. T.; Seeberger, P. H. J. Org. Chem. 2013, 78, 6384–6389; (c) Tsubogo, T.; Ishiwata, T.; Kobayashi, S. Angew. Chem., Int. Ed. 2013, 52, 6590–6604; (d) Chan, N.; Cunningham, M. F.; Hutchinson, R. A. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3081–3096; (e) Ahao, D.; Ding, K. ACS Catal. 2013, 3, 928–944; (f) Itabaiana, I. Jr., Soter de Mariz e Miranda, L.; Alves de Souza, R. O. M. J. Mol. Catal. B: Enzym. 2013, 85–86, 1–9; (g) Hessel, V.; Gürsel, I. V.; Wang, Q.; Noël, T.; Lang, J. Chem. Eng. Technol. 2012, 35, 1184–1204; (h) Hartman, R. L. Org. Process Res. Dev. 2012, 16, 870–887; (i) Oelgemöller, M. Chem. Eng. Technol. 2012, 35, 1144–1152; (j) McPake, C. B.; Sanford, G. Org. Process Res. Dev. 2012, 16, 844–851; (k) Wegner, J.; Ceylan, S.; Kirschning, A. Adv. Synth. Catal. 2012, 354, 17–57; (l) Mawatari, K.; Kazoe, Y.; Aota, A.; Tsukahara, T.; Sato, K; Kitamori, T. J. Flow. Chem. 2011, 1, 3–12; (m) Noël, T.; Buchwald, S. F. Chem. Soc. Rev. 2011, 40, 5010–5029; (n) Wegner, J.; Ceylan, S.; Kirschning, A. Chem. Commun. 2011, 47, 4583–4592; (o) Rebrov, E. V.; Schouten, J. C.; de Croon, M. H. J. M. Chem. Eng. Sci. 2011, 66, 1374–1393.

  • For selected reviews, see: (a) Aijaz, A.; Xu, Q. J. Phys. Chem. Lett. 2014, 5, 1400–1411; (b) Miyamura, H.; Kobayashi, S. Acc. Chem. Res. 2014, 47, 1054–1066; (c) Shuit, S. H.; Yee, K. F.; Lee, K. T.; Subhash, B.; Tan, S. H. RSC. Adv. 2013, 3, 9070–9094; (d) Anderson, E. B.; Buchmeiser, M. R. ChemCatChem 2012, 4, 30–44; (e) Sahoo, S.; Bordoloi, A.; Halligudi, S. B. Catal. Surv. Asia 2011, 15, 200–214; (f) Harris, K. D. M.; Thomas, J. M. ChemCatChem 2009, 1, 223–231; (g) Matsumoto, T.; Ueno, M.; Wang, N.; Kobayashi, S. Chem. Asian J. 2008, 3, 196–214.

  • For selected examples of hydrogenation reaction of nitro compounds under continuous-flow conditions, see: (a) Chen, J.; Przyuski, K.; Roemmele, R.; Bakale, R. P. Org. Process. Res. Dev. ASAP; (b) Javaid, R.; Kawasaki, S-i.; Suzuki, A.; Suzuki, T. M. Beilstein J. Org. Chem. 2013, 9, 1156–1163; (c) Baumann, M.; Baxendale, I. R.; Ley, S. V. Synlett, 2010, 749–752; (d) Jones, R. V.; Godorhazy, L.; Varga, N.; Szalay, D.; Urge, L.; Darvas, F. J. Comb. Chem. 2006, 8, 110–116; (e) Kreutzer, M. T.; Kapteijn, F.; Moulijn, J. A. Catal. Today 2005, 105, 421–428; (f) Solodenko, W.; Wen, H.; Leue, S.; Stuhlmann, F.; Sourkouni-Argirusi, G.; Jas, G.; Schönfeld, H.; Kunz, U.; Kirschning, A. Eur. J. Org. Chem. 2004, 3601–3610; (g) Hatziantoniou, V.; Andersson, B.; Schöön, N.-H. Ind. Eng. Chem. Process Des. Dev. 1986, 25, 964–970.

  • The catalyst was packed in a range of column types, see: (a) Tsubogo, T.; Yamashita, Y.; Kobayashi, S. Top. Catal. 2014, 57, 935–939; (b) Tsubogo, T.; Yamashita, Y.; Kobayashi, S. Chem. Eur. J. 2012, 18, 13624–13628; (c) Kaizuka, K.; Lee, K.-Y.; Miyamura, H.; Kobayashi, S. J. Flow Chem. 2012, 2, 1–4; (d) Oyamada, H.; Naito, T.; Kobayashi, S. Beilstein J. Org. Chem. 2011, 7, 735–739; (e) Kobayashi, S.; Miyamura, H.; Akiyama, R.; Ishida, T. J. Am. Chem. Soc. 2005, 127, 9251–9254. See also: O'Brien, M.; Taylor, N.; Polyzos, A.; Baxendale, I. R.; Ley, S. V. Chem. Sci. 2011, 2, 1250–1257.

  • The catalyst was immobilized on the surface of a capillary type column, see: (a) Wang, N.; Matsumoto, T.; Ueno, M.; Miyamura, H.; Kobayashi, S. Angew. Chem., Int. Ed. 2009, 48, 4744–4746; (b) Ueno, M.; Suzuki, T.; Naito, T.; Oyamada, H.; Kobayashi, S. Chem. Commun. 2008, 1647–1649; (c) Kobayashi, J.; Mori, Y.; Kobayashi, S. Adv. Synth. Catal. 2005, 347, 1889–1892.

  • The catalyst was immobilized on the glass surface of a microchannel reactor type column, see: (a) Kobayashi, J.; Mori, Y.; Kobayashi, S. Chem. Commun. 2005, 2567–2568; (b) Kobayashi, J.; Mori, Y.; Okamoto, K.; Akiyama, R.; Ueno, M.; Kitamori, T.; Kobayashi, S. Science, 2004, 304, 1305–1308.

  • (a) Oyamada, H.; Naito, T.; Miyamoto, S.; Akiyama, R.; Hagio, H.; Kobayashi, S. Org. Biomol. Chem. 2008, 6, 61–65; (b) Oyamada, H.; Akiyama, R.; Hagio, H.; Naito, T.; Kobayashi, S. Chem. Commun. 2006, 4297–4299.

  • Tokyo Chemical Industry Co. Ltd. (TCI) or JGC C&C.