Linkage Chemistry of S(VI) Fluorides.

Daming Zeng, Wei-Ping Deng, Xuefeng Jiang

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 2023;29(33):e202300536

PMID: 36959094

Abstract

Sulfur(VI)-fluoride exchange linkage as a next generation of click chemistry was introduced by Sharpless and coworkers in 2014. Distinguished from CuAAC, the SuFEx reaction proceeds under metal-free conditions, and the reactive linkers are variable, enabling access to a diverse class of linkage compounds. Therein, a series of SuFEx linkers emerged has been widely prevalent in diverse fields. The S -F bond in comparison to S -Cl bond features excellent stability and chemoselectivity. The linkage chemistry primarily involves the formation of S-O and S-N bonds via commercially available phenols and amines, yet less study on C-SuFEx linkage. This review will focus on three types of linkage for SuFEx linkers comprising S-O, S-N, and S-C bonds, and we hope to provide a practical guidance for SuFEx linkage chemistry.

Address: Shanghai Frontiers Science Center, of Optogenetic Techniques for Cell Metabolism, School of Pharmacy, East China University of Science and Technology, Shanghai, 200237, China.; Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Rd., Shanghai, 200062, P. R. China.

DOI: 10.1002/chem.202300536

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https://doi.org/10.1002/chem.202300536

MeSH Terms: Fluorides, Click Chemistry, Sulfur, Polymers, Nitrogen