Fe(II)/Fe(III)-Catalyzed Intramolecular Didehydro-Diels–Alder Reaction of Styrene-ynes

The intramolecular didehydro-Diels–Alder reaction of styrene-ynes was catalyzed by Fe­(II) and Fe­(III) to produce various naphthalene derivatives under microwave heating conditions. Mechanistic calculations found that the Fe­(II) catalyst activates the styrenyl diene in an inverse-electron-demand D...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-02, Vol.83 (3), p.1196-1203
Main Authors: Mun, Hyeon Jin, Seong, Eun Young, Ahn, Kwang-Hyun, Kang, Eun Joo
Format: Article
Language:English
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Summary:The intramolecular didehydro-Diels–Alder reaction of styrene-ynes was catalyzed by Fe­(II) and Fe­(III) to produce various naphthalene derivatives under microwave heating conditions. Mechanistic calculations found that the Fe­(II) catalyst activates the styrenyl diene in an inverse-electron-demand Diels–Alder reaction, and the consecutive dehydrogenation reaction can be promoted by either Fe­(II)-catalyzed direct dehydrogenation or an Fe­(III)-catalyzed rearomatization/dehydrogenation pathway.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02672