Metallaphotoredox-Catalyzed Three-Component Couplings for Practical Synthesis of Ureas and Carbamates
作者机构：Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon ReductionMinistry of EducationCollege of ChemistryCentral China Normal University152 Luoyu RoadWuhanHubei430079 China Wuhan Youji Industries Co.LtdNo.1 2nd Chemical Rd.WuhanHubei430082 China Hubei Key Laboratory of Purification and Application of Plant Anti-cancer Active IngredientsSchool of Chemistry and Life SciencesHubei University of EducationWuhanHubei430205 China State Key Laboratory for Oxo Synthesis and Selective OxidationLanzhou Institute of Chemical PhysicsChinese Academy of SciencesLanzhouGansu730000 China School of Chemistry and Chemical EngineeringHenan Normal UniversityXinxiangHenan453007 China Wuhan Institute of Photochemistry and TechnologyWuhanHubei430082 China State Key Laboratory of Organometallic ChemistryShanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai200032 China
出 版 物：《Chinese Journal of Chemistry》 (中国化学（英文版）)
年 卷 期：2024年第42卷第3期
页 面：264-270页
核心收录：
学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学]
基 金：the National Natural Science Foundation of Chinaa(Nos.22271113,92256301,21822103,91956201,21820102003 and 21602052) the Natural Science Foundation of Hubei Province(No.2022CFB413) the fund from Central China Normal University for support of this research
主 题：Cross-coupling Nickel Photoredox catalysis Three-component reaction Ureas Carbamates
摘 要：Ureas are widely used in drugs,materials and catalysts because of their diamide structure,which can form strong hydrogen ***,it is of great scientific significance to develop efficient and green methods for the synthesis of urea compounds,especially unsymmetrical ***,we have disclosed novel and highly efficient three-component coupling reactions of organic halides,sodium cyanate and amines enabled by nickel/photoredox dual catalysis for the preparation of unsymmetrical *** reaction features simple and safe operations,broad substrate scopes,and product *** allows the facile synthesis of N-aryl/vinyl ureas from readily available,user-friendly feedstocks under mild conditions(27 examples,36%—98%yields).In addition,this method is further derived to alcohols as nucleophiles to synthesize a series of carbamates(15 examples,40%—95%yields).The mechanism experiment shows that the isocyanate produced by the coupling of halide and sodium cyanate may be the key intermediate in this reaction.
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