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

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

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

Rashed, Md Nurnobi; Touchy, Abeda Sultana; Chaudhari, Chandan et al.

Chinese journal of catalysis, 2020, 41(6), 970-976

Permalink : https://hdl.handle.net/2115/85825

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アクセス権	open access
URI	https://hdl.handle.net/2115/85825
タイトル	Selective C3-alkenylation of oxindole with aldehydes using heterogeneous CeO2 catalyst
著者	Rashed, Md Nurnobi ; Touchy, Abeda Sultana ; Chaudhari, Chandan ; Jeon, Jaewan ; Siddiki, S. M. A. Hakim ; Toyao, Takashi ; Shimizu, Ken-ichi
著者名 Rashed, Md Nurnobi
著者名 Touchy, Abeda Sultana
著者名 Chaudhari, Chandan
著者名 Jeon, Jaewan
著者名 Siddiki, S. M. A. Hakim
e-Rad_Researcher 80775388 著者名 Toyao, Takashi
e-Rad_Researcher 60324000 著者名 Shimizu, Ken-ichi
言語	英語
キーワード	Oxindole
	Aldehyde
	Aldol condensation
	C3-alkenylation
	CeO2 catalyst
発行日	2020-06
出版者	Science Press
収録物名	Chinese journal of catalysis
巻(号)	41(6)
ページ	970-976
抄録	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.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
権利情報	Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International
権利情報	© 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/
PISSN	0253-9837
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1016/S1872-2067(19)63515-1