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Synthesis 2025; 57(04): 883-890
DOI: 10.1055/a-2492-4375
DOI: 10.1055/a-2492-4375
paper
N-(Trimethylsilyl)diethylamine-Promoted Intramolecular SNAr Reaction of Electron-Rich Aryl Fluorides
This work was supported by Japan Society for the Promotion of Science (JSPS) KAKENHI (Grant No. 20K15468).
Abstract
N-(Trimethylsilyl)diethylamine (TMSNEt2) significantly promotes intramolecular nucleophilic aromatic substitution (SNAr) reactions of electron-rich aryl fluorides with t-BuOK and crown ether. Although substrates bearing electron-donating groups are conventionally inert under SNAr conditions, the activation of substrates by TMSNEt2 enables the reactions to proceed even at room temperature. This method is applicable to the preparation of benzo-fused oxygen-containing heterocycles, such as 3,4-dihydro-2H-1,4-benzoxazines, 3,4-dihydro-2H-1,5-benzoxazepines, and 3,4-dihydro-2H-1-benzopyran, in good to excellent yields (56–93%).
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2492-4375.
- Supporting Information
Publication History
Received: 26 October 2024
Accepted after revision: 28 November 2024
Accepted Manuscript online:
28 November 2024
Article published online:
22 January 2025
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