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Selective C3-alkenylation of oxindole with aldehydes using heterogeneous CeO2 catalyst
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| Title: | Selective C3-alkenylation of oxindole with aldehydes using heterogeneous CeO2 catalyst |
| Authors: | Rashed, Md Nurnobi Browse this author | | Touchy, Abeda Sultana Browse this author | | Chaudhari, Chandan Browse this author | | Jeon, Jaewan Browse this author | | Siddiki, S. M. A. Hakim Browse this author | | Toyao, Takashi Browse this author →KAKEN DB | | Shimizu, Ken-ichi Browse this author →KAKEN DB |
| Keywords: | Oxindole | | Aldehyde | | Aldol condensation | | C3-alkenylation | | CeO2 catalyst |
| Issue Date: | Jun-2020 |
| Publisher: | Science Press |
| Journal Title: | Chinese journal of catalysis |
| Volume: | 41 |
| Issue: | 6 |
| Start Page: | 970 |
| End Page: | 976 |
| Publisher DOI: | 10.1016/S1872-2067(19)63515-1 |
| Abstract: | We report herein that a commercially available CeO2 is an active and reusable catalyst for the C3-selective alkenylation of oxindole with aldehydes under solvent-free conditions. This. catalytic method is generally applicable to different aromatic and aliphatic aldehydes, giving 3-alkyledene-oxindoles in high yields (87%-99%) and high stereoselectivities (79%-93% to E-isomers). This is the first example of the catalytic synthesis of 3-alkenyl-oxindoles from oxindole and various aliphatic aldehydes. The Lewis acid-base interaction between Lewis acid sites on CeO2 and benzaldehyde was studied by in situ IR. The structure-activity relationship study using CeO2 catalysts with different sizes suggests that defect-free CeO2 surface is the active site for this reaction. (C) 2020, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved. |
| Rights: | © 2020. This manuscript version is made available under the CC-BY-NC-ND 4.0 license https://creativecommons.org/licenses/by-nc-nd/4.0/ | | https://creativecommons.org/licenses/by-nc-nd/4.0/ |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/85825 |
| Appears in Collections: | 触媒科学研究所 (Institute for Catalysis) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 鳥屋尾 隆
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