N -Alkylsulfonamide Nucleophilicity: Experimental and Computational Assessment of Nitrogen Nucleophilicity of ( S )-2-(Iodomethyl)-1-tosylpyrrolidine

Organic Letters 2026

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Authors: Julien Escudero, Tomohiro Yasukawa, Pengchen Ma, Pauline Bianchi, Zhitian Wang, Véronique Bellosta, Kendall N. Houk, Janine Cossy
DOI: 10.1021/acs.orglett.5c05226
Cited by: 0
References: 24

Abstract

Sulfonamides are generally considered to be non-nucleophilic due to the presence of a sulfonyl group. We show that N -alkylsulfonamides are sufficiently basic/nucleophilic to be protonated and react with electrophilic centers. Contrasts with N- and O-reactivities of amides are made for intramolecular iodoamidations of alkenes. The nucleophilicity of nitrogen of ( S )-2-(iodomethyl)-1-tosylpyrrolidine was confirmed experimentally and by DFT calculation.

Fields of Study & Subjects

Chemical Reaction Mechanisms Advanced Synthetic Organic Chemistry Asymmetric Synthesis and Catalysis

Publication details

Journal / source
Organic Letters
Volume
28
Issue
5
Pages
1727–1731
Publication date
28 January 2026
Language
EN