Rapid and chemoselective imidation of sulfides in aqueous buffer enabled by a novel guanidine-derived N-O reagent  

作　　者：Hanzheng Li Long Xu Jiajia Dong 

机构地区：[1]Key Laboratory of Organofluorine Chemistry,Center for Excellence in Molecular Synthesis,Shanghai Institute of Organic Chemistry,University of Chinese Academy of Sciences,Chinese Academy of Sciences,Shanghai,200032,China [2]Institute of Translational Medicine,National Facility for Translational Medicine(Shanghai),Shanghai Jiao Tong University,Shanghai,200240,China [3]School of Chemistry and Chemical Engineering,Zhangjiang Institute for Advanced Study,Shanghai Jiao Tong University,Shanghai,200240,China [4]Shanghai Artificial Intelligence Laboratory,Shanghai,200232,China

出　　处：《Science China Chemistry》2024年第6期1929-1934,共6页中国科学（化学英文版）

基　　金：supported by the Ministry of Science and Technology of China,Major State Basic Research Development Program of China(2023YFA1506500,2021YFF0701704);Shanghai Pilot Program for Basic Research,Shanghai Jiao Tong University(21TQ1400223);WLA Laboratories for the financial support。

摘　　要：Herein we report the facile synthesis of a series of novel N-O reagents and identify N′-di-Boc-N′′-[(mesitylsulfonyl)oxy]-guanidine as an efficient imidating reagent.This reagent is synthetically scalable and bench-stable,yet it shows unprecedented reactivity and chemoselectivity towards S(II)in buffer/hexafluoroisopropanol(HFIP)system,to generate a new class of Nguanyl sulfilimines.Further transformation of N-guanyl sulfilimines to N-guanyl sulfoximines provides us a chance to investigate these rarely reached compounds,which are shown to be versatile precursors to a variety of N-heterocyclic and NHsulfoximines.Our work provides an addition to the tool box of both sulfur imidation and guanidine synthesis,especially for the need of rapid and selective modifications of sulfur(II)center under biocompatible conditions.

关 键 词：sulfur imidation N-O reagent 

分 类 号：TQ421.12[化学工程]