Synthesis 2023; 55(19): 3121-3128
DOI: 10.1055/s-0042-1751466
paper

Synthesis of Aliphatic Nitriles via Desulfonylative Smiles Rearrangement

Masahiro Abe
,
Honoka Jitsumatsu
,
Mikoto Araki
,
Akiho Mizukami
,
Tetsutaro Kimachi
,
Kiyofumi Inamoto

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.

Supporting Information



Publikationsverlauf

Eingereicht: 26. April 2023

Angenommen nach Revision: 25. Mai 2023

Artikel online veröffentlicht:
28. Juni 2023

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