Photoredox-Catalyst-Free Carboxylation of Unactivated Alkenes in DMSO: Synthesis of Polycyclic Indole Derivatives and Aliphatic Acids

A new method for the carboxylation of unactivated alkenes using CO<sub>2</sub> radical anions in the absence of a photoredox catalyst has been developed. The photocatalyst-free approach enables the efficient synthesis of polycyclic indole derivatives and linear carboxylic acids under mild conditions from HCO<sub>2</sub>K with/without 1,4-diazabicyclo[2.2.2]octane (DABCO) in DMSO. This work demonstrates a significant advance in green chemistry, showcasing a catalyst-free approach for the functionalization of unactivated alkenes with cheap and readily available HCO<sub>2</sub>K.

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Publication Details

Journal
Organic Letters
Published
2024-12-06
DOI
https://doi.org/10.1021/acs.orglett.4c04051
Citations
11
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
2.75

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article

Photoredox-Catalyst-Free Carboxylation of Unactivated Alkenes in DMSO: Synthesis of Polycyclic Indole Derivatives and Aliphatic Acids

Tsuyoshi Mita, Kosaku Tanaka, Wataru Kanna, Yamato Ueno et al.
11 citations
Organic Letters
Radical Photochemical Reactions
2.75
article

Photoredox-Catalyst-Free Carboxylation of Unactivated Alkenes in DMSO: Synthesis of Polycyclic Indole Derivatives and Aliphatic Acids

Tsuyoshi Mita, Kosaku Tanaka, Wataru Kanna, Yamato Ueno, Hiroki Hayashi, Suvankar Debbarma
article en
11 citations

Abstract

A new method for the carboxylation of unactivated alkenes using CO<sub>2</sub> radical anions in the absence of a photoredox catalyst has been developed. The photocatalyst-free approach enables the efficient synthesis of polycyclic indole derivatives and linear carboxylic acids under mild conditions from HCO<sub>2</sub>K with/without 1,4-diazabicyclo[2.2.2]octane (DABCO) in DMSO. This work demonstrates a significant advance in green chemistry, showcasing a catalyst-free approach for the functionalization of unactivated alkenes with cheap and readily available HCO<sub>2</sub>K.

Organic LettersVol. 26(50)
Hokkaido University (JP)
Tokyo Ohka Foundation for The Promotion of Science and Technology, Japan Society for the Promotion of Science, Exploratory Research for Advanced Technology
Openalex Percentile: Top 9%
Radical Photochemical Reactions
2.75
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Photoredox-Catalyst-Free Carboxylation of Unactivated Alkenes in DMSO: Synthesis of Polycyclic Indole Derivatives and Aliphatic Acids — Tsuyoshi Mita, Kosaku Tanaka, et al. · Organic Letters (2024) | TGRS Research Map | TGRS