Photo-Promoted Decarboxylative Arylation of 3-Indoleacetic Acids for the Synthesis of Indole-Containing Diarylmethanes

A visible-light-driven, photocatalyst-free C-C bond formation strategy is reported, enabling the decarboxylative arylation of 3-indoleacetic acid with (hetero)aromatic nitriles via electron donor-acceptor (EDA) complex activation. In addition, this strategy is also applicable to the coupling reaction between 3-indoleacetic acids and 2-sulfonylated benzothiazoles. Diverse indole-containing diarylmethanes were afforded in moderate to excellent yields. Moreover, biological evaluation revealed that several products exhibited antiproliferative activity against B16, HCT116, and HepG2 cancer cell lines. This protocol features mild conditions and a broad substrate scope and avoids external photocatalysts, offering a practical approach for constructing indole-based bioactive scaffolds.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-03-11
DOI
https://doi.org/10.1021/acs.joc.5c03166
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Photo-Promoted Decarboxylative Arylation of 3-Indoleacetic Acids for the Synthesis of Indole-Containing Diarylmethanes

Jia‐Yi Wang, Xiaodong Tang, Xu Wu, Jie Li et al.
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Photo-Promoted Decarboxylative Arylation of 3-Indoleacetic Acids for the Synthesis of Indole-Containing Diarylmethanes

Jia‐Yi Wang, Xiaodong Tang, Xu Wu, Jie Li, Weiya Kong, X Q Yao
article en

Abstract

A visible-light-driven, photocatalyst-free C-C bond formation strategy is reported, enabling the decarboxylative arylation of 3-indoleacetic acid with (hetero)aromatic nitriles via electron donor-acceptor (EDA) complex activation. In addition, this strategy is also applicable to the coupling reaction between 3-indoleacetic acids and 2-sulfonylated benzothiazoles. Diverse indole-containing diarylmethanes were afforded in moderate to excellent yields. Moreover, biological evaluation revealed that several products exhibited antiproliferative activity against B16, HCT116, and HepG2 cancer cell lines. This protocol features mild conditions and a broad substrate scope and avoids external photocatalysts, offering a practical approach for constructing indole-based bioactive scaffolds.

The Journal of Organic ChemistryVol. 91(12)
Guangdong Pharmaceutical University (CN), Southern Medical University (CN)
Openalex Percentile: Top 25%
Radical Photochemical Reactions
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