Template-Directed Selective Photodimerization Reactions of 5‑Arylpenta-2,4-dienoic Acids

We developed an efficient method that enables selective photodimerization of 5-arylpenta-2,4-dienoic acids (i.e., vinylogous cinnamic acids). The use of 1,8-dihydroxynaphthalene as a template ensures proximity of the two reacting olefins so that irradiation of template-bound dienoic acids gives mono...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-07, Vol.89 (14), p.10409-10418
Main Authors: Munir, Badar, Yagci, Bilge Banu, Zorlu, Yunus, Türkmen, Yunus E.
Format: Article
Language:English
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Summary:We developed an efficient method that enables selective photodimerization of 5-arylpenta-2,4-dienoic acids (i.e., vinylogous cinnamic acids). The use of 1,8-dihydroxynaphthalene as a template ensures proximity of the two reacting olefins so that irradiation of template-bound dienoic acids gives mono [2 + 2] cycloaddition products in good to excellent yields (up to 99%), as single regioisomers, and with high diastereoselectivities (dr = 3:1 to 13:1). The geometrical and stereochemical features of compounds 12a, 16a, and 22a were analyzed by X-ray crystallography.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01374