Work

Electrochemical Conversions of Sulfenamides into Sulfonimidoyl- and Sulfondiimidoyl Fluorides

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide The invention of versatile linkage agents provides the chemical basis for SuFEx chemistry. Sulfonimidoyl fluorides and sulfondiimidoyl fluorides are aza-isosteres of sulfonyl fluorides with diverse reactivity through the fine-tuning of N -substituents. However, limited synthetic approaches impede their wide applications in SuFEx chemistry. Herein, we develop a straightforward electrochemical strategy for sulfonimidoyl- and sulfondiimidoyl fluorides through sequential oxidations of the readily available sulfenamides via sulfinamide and iminosulfinamide intermediates, respectively. The previously rarely investigated (bis)sulfondiimidoyl fluorides are now easily accessible and readily participate in SuFEx chemistry with diverse oxygen and nitrogen nucleophiles, macrocyclization, and polymerization.

Source: JACS Au

DOI: 10.1021/jacsau.5c00374

Authors: Bin Zhao, Ding-Bo Zeng, Xinglei He, Jing-Heng Li, Yuqi Lin, Ke-Yin Ye

Institutions: Fuzhou University, Henan Normal University

Language: English

Topic: Sulfur-Based Synthesis Techniques

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,500

Funders: Henan Normal University, National Natural Science Foundation of China, Fuzhou University