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Nitrile Synthesis via Desulfonylative-Smiles Rearrangement

Masahiro Abe*, Sayasa Nitta, Erina Miura, Tetsutaro Kimachi and Kiyofumi Inamoto*

*Mukogawa Women's University, 11-68, 9-Bancho, Koshien, Nishinomiya, Hyogo 663-8179, Japan, Email:,

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

DOI: 10.1021/acs.joc.1c03011

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A simple base-promoted intramolecular nucleophilic aromatic substitution of N-[(2-nitrophenyl)sulfonyl]benzamides provides nitriles in very good yields under redox-neutral conditions and avoids the use of toxic cyanide species and transition metals. This process shows broad scope and tolerates various functional groups.

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proposed mechanism

Synthesis of Aliphatic Nitriles via Desulfonylative Smiles Rearrangement

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

Key Words


ID: J42-Y2022