多相CeO2催化剂上氧化吲哚与醛的选择性C3烯基化反应

doi:10.1016/S1872-2067(19)63515-1

催化学报 ›› 2020, Vol. 41 ›› Issue (6): 970-976.DOI: 10.1016/S1872-2067(19)63515-1

多相CeO₂催化剂上氧化吲哚与醛的选择性C3烯基化反应

Md. Nurnobi Rashed^a, Abeda Sultana Touchy^a, Chandan Chaudhari^b, Jaewan Jeon^a, S. M. A. Hakim Siddiki^a, Takashi Toyao^a,c, Ken-ichi Shimizu^a,c

a 北海道大学催化科学研究所, N-21, W-10, 札幌001-0021, 日本;
b 名古屋大学工程研究生院, 化学系统工程系, 名古屋464-8603, 日本;
c 京都大学催化剂与电池元素战略基地, 桂校区, 京都615-8520, 日本

收稿日期:2019-07-30 修回日期:2019-09-18 出版日期:2020-06-18 发布日期:2020-01-21
通讯作者: S. M. A. Hakim Siddiki, Ken-ichi Shimizu
基金资助:
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.

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

Md. Nurnobi Rashed^a, Abeda Sultana Touchy^a, Chandan Chaudhari^b, Jaewan Jeon^a, S. M. A. Hakim Siddiki^a, Takashi Toyao^a,c, Ken-ichi Shimizu^a,c

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:2019-07-30 Revised:2019-09-18 Online:2020-06-18 Published:2020-01-21
Contact: S1872-2067(19)63515-1
Supported by:
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.

摘要/Abstract

摘要： 本文报道了将市售CeO₂作为一种高活性和可重复使用的催化剂用于无溶剂条件下氧化吲哚与醛的C3选择性烷基化反应.这种催化方法一般适用于不同的芳香族和脂肪族醛，得到3-烷基二烯-辛醇，产率高（87%-99%），立体选择性高（79%-93%为E-异构体）.这是从氧化吲哚与各种脂肪族醛催化合成3-烯基氧化吲哚的首例.采用原位红外光谱研究了CeO₂上Lewis酸位点与苯甲醛之间的Lewis酸-碱相互作用.不同粒径CeO₂催化剂的构效关系研究表明，无缺陷CeO₂表面是该反应的活性中心.

关键词: 氧化吲哚, 醛, 羟醛缩合, C3-烯基化, 二氧化铈催化剂

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.

Key words: Oxindole, Aldehyde, Aldol condensation, C3-alkenylation, CeO₂ catalyst

Md. Nurnobi Rashed, Abeda Sultana Touchy, Chandan Chaudhari, Jaewan Jeon, S. M. A. Hakim Siddiki, Takashi Toyao, Ken-ichi Shimizu. 多相CeO₂催化剂上氧化吲哚与醛的选择性C3烯基化反应[J]. 催化学报, 2020, 41(6): 970-976.

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.

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多相CeO₂催化剂上氧化吲哚与醛的选择性C3烯基化反应

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

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