Citation: Md. Nurnobi Rashed, Abeda Sultana Touchy, Chandan Chaudhari, Jaewan Jeon, S. M. A. Hakim Siddiki, Takashi Toyao, Ken-ichi Shimizu. Selective C3-alkenylation of oxindole with aldehydes using heterogeneous CeO₂ catalyst[J]. Chinese Journal of Catalysis, ;2020, 41(6): 970-976. doi: S1872-2067(19)63515-1 shu

Selective C3-alkenylation of oxindole with aldehydes using heterogeneous CeO₂ catalyst

a Institute for Catalysis, Hokkaido University, N-21, W-10, Sapporo 001-0021, Japan;
b Department of Chemical Systems Engineering, Graduate School of Engineering, Nagoya University, Nagoya 464-8603, Japan;
c Elements Strategy Initiative for Catalysts and Batteries, Kyoto University, Katsura, Kyoto 615-8520, Japan

Received Date: 30 July 2019
Revised Date: 18 September 2019

Fund Project: This study was supported financially by a series of JSPS KAKENHI grants:17H01341, 18K14051, 18K14057, and 19K05556 from the Japan Society for the Promotion of Science (JSPS) and by the Japanese Ministry of Education, Culture, Sports, Science, and Technology (MEXT) within the projects "Integrated Research Consortium on Chemical Sciences (IRCCS)" and "Elements Strategy Initiative to Form Core Research Center", as well as by the JST-CREST project JPMJCR17J3.

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.
- Oxindole,
- Aldehyde,
- Aldol condensation,
- C3-alkenylation,
- CeO₂ catalyst
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
12. [12]
13. [13]
14. [14]
15. [15]
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
21. [21]
22. [22]
23. [23]
24. [24]
25. [25]
26. [26]
27. [27]
28. [28]
29. [29]
30. [30]
31. [31]
32. [32]
33. [33]
34. [34]
35. [35]
36. [36]
37. [37]
38. [38]
39. [39]
1. [1]
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沈阳化工大学材料科学与工程学院沈阳 110142

Selective C3-alkenylation of oxindole with aldehydes using heterogeneous CeO2 catalyst

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通讯作者: 陈斌, bchen63@163.com

Selective C3-alkenylation of oxindole with aldehydes using heterogeneous CeO₂ catalyst