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Published on: May 21, 2019
Visible-light-induced [4 + 2] cycloaddition of pentafulvenes by organic photoredox catalysis
Kenta Tanaka1, Yosuke Asada2, Yujiro Hoshino2
1Faculty of Pharmaceutical Science, Tokyo University of Science, 2641 Yamazaki, Noda-city, Chiba 278-8510, Japan. ktanaka@rs.tus.ac.jp.
Abstract:
We have developed thioxanthylium photoredox catalyzed [4 + 2] cycloaddition of pentafulvenes at room temperature under green light irradiation, which affords tetrahydrocyclopenta[b]chromenes with high regioselectivities. The present reaction provides a sustainable approach to carry out the cycloaddition of pentafulvenes without the use of transition metal catalysts or high-temperature conditions. This procedure enables a mild and straightforward access to 1,3a,9,9a-tetrahydrocyclopenta[b]chromenes. The quantum yield of the reaction (Φ = 0.15) indicates that the reaction would mainly proceed via photocatalytic pathways.
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