期刊
TETRAHEDRON
卷 137, 期 -, 页码 -出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2023.133394
关键词
Bronsted acid; Michael addition; Cascade cyclization; Ketone; Azadiene
A TfOH-catalyzed direct Michael addition and cascade cyclization reactions of azadienes with unactivated ketones have been developed, providing a divergent approach to 2,3-disubstituted benzofurans and benzofuro[3,2-b]pyridines. This method utilizes the weak nucleophilicity of unactivated ketones and controls the catalyst acidity as a key parameter. The use of commercial ketones and mild reaction conditions also offer synthetic and environmentally benign advantages.
TfOH-catalyzed direct Michael addition and cascade cyclization reactions of azadienes with unactivated ketones have been developed by controlling the amount of TfOH, which provide a divergent approach to 2,3-disubstituted benzofurans and benzofuro[3,2-b]pyridines. Due to their weak nucleophilicity, unac-tivated ketones are used for the first time to react with azadienes instead of preactivated carbonyl compounds, in which the catalyst acidity is a key parameter. This approach with commercial ketones in mild reaction conditions shows synthetic and environmentally benign advantages including metal-free catalyst, atom economy and simple operation.(c) 2023 Elsevier Ltd. All rights reserved.
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