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Efficient chemoselective hydrogenation of organic azides catalyzed by palladium nanoparticles with alkyne-derived homogeneous supports
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| Title: | Efficient chemoselective hydrogenation of organic azides catalyzed by palladium nanoparticles with alkyne-derived homogeneous supports |
| Authors: | Arai, Noriyoshi Browse this author | | Onodera, Nozomi Browse this author | | Ohkuma, Takeshi Browse this author →KAKEN DB |
| Keywords: | Palladium | | Nanoparticles | | Hydrogenation | | Organic azide | | Chemoselective |
| Issue Date: | 14-Sep-2016 |
| Publisher: | Elsevier |
| Journal Title: | Tetrahedron Letters |
| Volume: | 57 |
| Issue: | 37 |
| Start Page: | 4183 |
| End Page: | 4186 |
| Publisher DOI: | 10.1016/j.tetlet.2016.08.002 |
| Abstract: | Catalytic chemoselective hydrogenation of organic azides using palladium nanoparticles stabilized by alkyne derivatives was studied. A broad range of aromatic and aliphatic azides were smoothly reduced to the corresponding amines in excellent yields with a quite small amount of the catalyst. Hydrogenation of 3-phenylpropylazide gave 3-phenylpropylamine almost quantitatively with a substrate-to-palladium molar ratio (S/Pd) of 12,900 under 8 atm of H-2. The reaction under 1 atm of H2 also proceeded smoothly with an S/Pd of 1000. Several reduction-sensitive functional groups, such as carbonyl, halide, benzylic OH, and aliphatic nitro were well tolerated under the reaction conditions. (C) 2016 Elsevier Ltd. All rights reserved. |
| Rights: | © 2016. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/ | | http://creativecommons.org/licenses/by-nc-nd/4.0/ |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/71461 |
| Appears in Collections: | 工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 大熊 毅
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