Synthesis of Aliphatic Nitriles via Desulfonylative Smiles Rearrangement

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

*Mukogawa Women's University, 11-68, 9-Bancho, Koshien, Nishinomiya, Hyogo 663-8179, Japan, Email: abe_111mukogawa-u.ac.jp, inamotomukogawa-u.ac.jp

M. Abe, H. Jitsumatsu, M. Araki, A. Mizukami, T. Kimachi, K. Inamoto, Synthesis, 2023, 55, 3121-3128.

DOI: 10.1055/a-0042-1751466

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Abstract

A desulfonylative Smiles rearrangement of N-acyl (2-nitrophenyl)sulfonamides provides aliphatic nitriles in very good yields using potassium acetate as base and 1,3-dimethyl-2-imidazolidinone as solvent. The methods avoids the use of toxic metal cyanides or transition metals and is suitable for large-scale reactions and one-pot syntheses starting from carboxylic acids and chlorides.

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Nitrile Synthesis via Desulfonylative-Smiles Rearrangement

M. Abe, S. Nitta, E. Miura, T. Kimachi, K. Inamoto, J. Org. Chem., 2022, 87, 4460-4467.

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Key Words

nitriles, Smiles rearrangement, metal-cyanide-free, redox-free, sulfonamides, one-pot process

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ID: J66-Y2023