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Issue 40, 2020
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Visible-light-induced [4 + 2] cycloaddition of pentafulvenes by organic photoredox catalysis

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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.

Graphical abstract: Visible-light-induced [4 + 2] cycloaddition of pentafulvenes by organic photoredox catalysis

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Supplementary files

Article information


Submitted
03 Jun 2020
Accepted
05 Aug 2020
First published
06 Aug 2020

Org. Biomol. Chem., 2020,18, 8074-8078
Article type
Communication

Visible-light-induced [4 + 2] cycloaddition of pentafulvenes by organic photoredox catalysis

K. Tanaka, Y. Asada, Y. Hoshino and K. Honda, Org. Biomol. Chem., 2020, 18, 8074
DOI: 10.1039/D0OB01151G

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