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 

作者机构：Key Laboratory of Organofluorine ChemistryCenter for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai200032China Institute of Translational MedicineNational Facility for Translational Medicine(Shanghai)Shanghai Jiao Tong UniversityShanghai200240China School of Chemistry and Chemical EngineeringZhangjiang Institute for Advanced StudyShanghai Jiao Tong UniversityShanghai200240China Shanghai Artificial Intelligence LaboratoryShanghai200232China 

出 版 物：《Science China Chemistry》 (中国科学（化学英文版）)

年 卷 期：2024年第67卷第6期

页      面：1929-1934页

核心收录：

学科分类：081702[工学-化学工艺] 08[工学] 0817[工学-化学工程与技术] 0703[理学-化学] 

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 

主　　题：sulfur imidation N-O reagent 

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 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 *** 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 *** 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.