Photoinduced Copper-Catalyzed Coupling of Acylsilanes with Indoles or Electron-Rich Arenes

Although the reactions of electrophilic Fischer-type metal siloxycarbenes catalytically generated in situ from acylsilanes with a single nucleophile have been documented, the coupling of acylsilanes with two nucleophiles remains unexplored. Herein, we demonstrate that acylsilanes can act as effective cationic carbyne equivalents under visible-light-driven copper catalysis, enabling their coupling with diverse indoles or electron-rich arenes. This strategy operates under mild, redox-neutral conditions and exhibits broad functional group compatibility. Furthermore, the protocol provides a versatile platform for synthesizing symmetric aryl(bisindolyl)methanes and unsymmetric triarylmethane derivatives with high efficiency.

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Publication Details

Journal
Organic Letters
Published
2025-06-11
DOI
https://doi.org/10.1021/acs.orglett.5c01732
Citations
1
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.94

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article

Photoinduced Copper-Catalyzed Coupling of Acylsilanes with Indoles or Electron-Rich Arenes

Pengfei Xia, Jian-Hong Fan, Cheng Liu, Jing Yuan et al.
1 citations
Organic Letters
Sulfur-Based Synthesis Techniques
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article

Photoinduced Copper-Catalyzed Coupling of Acylsilanes with Indoles or Electron-Rich Arenes

Pengfei Xia, Jian-Hong Fan, Cheng Liu, Jing Yuan, Jiao Zhou
article en
1 citations

Abstract

Although the reactions of electrophilic Fischer-type metal siloxycarbenes catalytically generated in situ from acylsilanes with a single nucleophile have been documented, the coupling of acylsilanes with two nucleophiles remains unexplored. Herein, we demonstrate that acylsilanes can act as effective cationic carbyne equivalents under visible-light-driven copper catalysis, enabling their coupling with diverse indoles or electron-rich arenes. This strategy operates under mild, redox-neutral conditions and exhibits broad functional group compatibility. Furthermore, the protocol provides a versatile platform for synthesizing symmetric aryl(bisindolyl)methanes and unsymmetric triarylmethane derivatives with high efficiency.

Organic LettersVol. 27(25)
Hunan Institute of Science and Technology (CN)
National Natural Science Foundation of China, Natural Science Foundation of Hunan Province
Openalex Percentile: Top 25%
Sulfur-Based Synthesis Techniques
0.94
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