Catalytic Flow Hydrogenation of Aromatic Nitro Compounds Using Polysilane-Supported Palladium

Author:

Ueno Masaharu,Morii Yasuharu,Uramoto Kiyoko,Oyamada Hidekazu,Mori Yuichiro,Kobayashi Shū

Publisher

Springer Science and Business Media LLC

Subject

Organic Chemistry,Fluid Flow and Transfer Processes,Chemistry (miscellaneous)

Reference8 articles.

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2. 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. ChemCatChem2012, 4, 30–44; (e) Sahoo, S.; Bordoloi, A.; Halligudi, S. B. Catal. Surv. Asia2011, 15, 200–214; (f) Harris, K. D. M.; Thomas, J. M. ChemCatChem2009, 1, 223–231; (g) Matsumoto, T.; Ueno, M.; Wang, N.; Kobayashi, S. Chem. Asian J. 2008, 3, 196–214.

3. 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. Today2005, 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.

4. 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.

5. 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.

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