Palladium-Catalyzed Intramolecular <i>meta</i> -C–H Arylation Assisted by Nitrile Templates Under Microwave-Accelerated Conditions Accessing Fluorene Frameworks

Although intermolecular <i>meta</i>-C-H arylation has been thoroughly studied and well established, the intramolecular version of <i>meta</i>-C-H arylation is still largely unexplored and offers exciting opportunities for future research. With these considerations, we describe a palladium-catalyzed intramolecular <i>meta</i>-C-H arylation of 3-(4-benzylphenyl)propanoates, enabled by both aliphatic and aromatic nitrile templates under microwave-assisted conditions. This approach provides an efficient alternative pathway to fluorene frameworks via template-directed <i>meta</i>-C-H arylation. The method afforded fluorene derivatives exclusively in good to excellent yields. Additionally, postsynthetic modifications are used to access cyclopenta[<i>b</i>]fluorenones.

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Publication Details

Journal
Organic Letters
Published
2026-02-26
DOI
https://doi.org/10.1021/acs.orglett.5c05320
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Palladium-Catalyzed Intramolecular meta -C–H Arylation Assisted by Nitrile Templates Under Microwave-Accelerated Conditions Accessing Fluorene Frameworks

Kurella Mounika, G V V Satyanarayana
Organic Letters
Catalytic C–H Functionalization Methods
article

Palladium-Catalyzed Intramolecular meta -C–H Arylation Assisted by Nitrile Templates Under Microwave-Accelerated Conditions Accessing Fluorene Frameworks

Kurella Mounika, G V V Satyanarayana
article en

Abstract

Although intermolecular <i>meta</i>-C-H arylation has been thoroughly studied and well established, the intramolecular version of <i>meta</i>-C-H arylation is still largely unexplored and offers exciting opportunities for future research. With these considerations, we describe a palladium-catalyzed intramolecular <i>meta</i>-C-H arylation of 3-(4-benzylphenyl)propanoates, enabled by both aliphatic and aromatic nitrile templates under microwave-assisted conditions. This approach provides an efficient alternative pathway to fluorene frameworks via template-directed <i>meta</i>-C-H arylation. The method afforded fluorene derivatives exclusively in good to excellent yields. Additionally, postsynthetic modifications are used to access cyclopenta[<i>b</i>]fluorenones.

Organic LettersVol. 28(10)
Indian Institute of Technology Hyderabad (IN)
Openalex Percentile: Top 41%
Catalytic C–H Functionalization Methods
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