Issue 40, 2020

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

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

Supplementary files

Article information

Article type
Communication
Submitted
03 Jun 2020
Accepted
05 Aug 2020
First published
06 Aug 2020

Org. Biomol. Chem., 2020,18, 8074-8078

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements