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DOI: 10.1055/s-0042-1751466
Synthesis of Aliphatic Nitriles via Desulfonylative Smiles Rearrangement
This work was supported by the Japan Society for the Promotion of Science (JSPS KAKENHI Grant Numbers JP22K06515 and JP23K14330).
Abstract
Herein, we demonstrate the synthesis of aliphatic nitriles from N-acyl (2-nitrophenyl)sulfonamides via a desulfonylative Smiles rearrangement. The developed reaction routes provide a variety of aliphatic nitriles containing primary, secondary, and tertiary carbon centers in good-to-excellent yields. Our method requires the use of the easy-to-handle reagent potassium acetate and solvent 1,3-dimethyl-2-imidazolidinone, and it does not rely on toxic metal cyanides or transition metals. The process is suitable for large-scale reaction and for one-pot syntheses starting from an acyl chloride or a carboxylic acid.
Key words
nitriles - Smiles rearrangement - metal-cyanide-free - redox-free - sulfonamides - one-pot processSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751466.
- Supporting Information
Publication History
Received: 26 April 2023
Accepted after revision: 25 May 2023
Article published online:
28 June 2023
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