A General Electrochemical Synthesis of Sulfonimidoyl Fluorides, Azides, and Acetates - Details

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Abstract：

Sulfonimidoyl　fluorides,　the　aza-bioisostere　of　sulfonyl　fluorides,　are　emerging　as　a　promising　linkage　agent　in　the　sulfur(VI)　fluoride　exchange　reaction　(SuFEx).　However,　conventional　synthetic　approaches　typically　require　the　use　of　either　unstable　sulfonimidoyl　chlorides,　toxic　and　corrosive　sulfur　fluorides,　or　expensive　electrophilic　fluorinating　agents.　Herein,　we　report　an　electrochemistry-enabled　oxidative　nucleophilic　fluorination　of　readily　available　and　bench-stable　sulfinamides　using　a　commercially　available　and　easy-to-handle　triethylamine　trihydrofluoride.　With　other　nucleophilic　agents,　this　electrochemical　approach　also　serves　as　a　general　approach　to　diverse　sulfonimidoyl　derivatives,　including　sulfonimidoyl　azides　and　acetates.　©　2024　Chinese　Chemical　Society.　All　rights　reserved.

Keyword：

click chemistry electrochemistry sulfinamide sulfonimidoyl fluoride sulfur (VI) fluoride exchange reaction

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[ 1 ] [Jiang Y.-M.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 2 ] [Lin Y.-Y.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 3 ] [Zhu L.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 4 ] [Yu Y.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 5 ] [Li Y.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 6 ] [Lin Y.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 7 ] [Ye K.-Y.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University, Fuzhou, 350108, China

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Source ：

CCS Chemistry

ISSN： 2096-5745

Year： 2024

Issue： 8

Volume： 6

Page： 2021-2030

9 . 4 0 0

JCR@2023

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