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

Kenta Tanaka; Yosuke Asada; Yujiro Hoshino; Kiyoshi Honda

doi:10.1039/d0ob01151g

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

Kenta Tanaka, Yosuke Asada, Yujiro Hoshino, Kiyoshi Honda

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

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.

Original language	English
Pages (from-to)	8074-8078
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	18
Issue number	40
DOIs	https://doi.org/10.1039/d0ob01151g
Publication status	Published - Oct 28 2020
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "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.",

author = "Kenta Tanaka and Yosuke Asada and Yujiro Hoshino and Kiyoshi Honda",

note = "Funding Information: We thank Prof. Mahito Atobe of Yokohama National University for cyclic voltammetry measurements. Funding for this research was provided by Yokohama National University (kyodo kenkyu suishin program B) and Nakatsuji Foresight Foundation (Nakatsuji Foresight Foundation Research Grant). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

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T1 - Visible-light-induced [4 + 2] cycloaddition of pentafulvenes by organic photoredox catalysis

AU - Tanaka, Kenta

AU - Asada, Yosuke

AU - Hoshino, Yujiro

AU - Honda, Kiyoshi

N1 - Funding Information: We thank Prof. Mahito Atobe of Yokohama National University for cyclic voltammetry measurements. Funding for this research was provided by Yokohama National University (kyodo kenkyu suishin program B) and Nakatsuji Foresight Foundation (Nakatsuji Foresight Foundation Research Grant). Publisher Copyright: © The Royal Society of Chemistry.

PY - 2020/10/28

Y1 - 2020/10/28

N2 - 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.

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

Abstract

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