首页|Metallaphotoredox-Catalyzed Three-Component Couplings for Practical Synthesis of Ureas and Carbamates

Metallaphotoredox-Catalyzed Three-Component Couplings for Practical Synthesis of Ureas and Carbamates

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Ureas are widely used in drugs,materials and catalysts because of their diamide structure,which can form strong hydrogen bonds.Therefore,it is of great scientific significance to develop efficient and green methods for the synthesis of urea compounds,especially unsymmetrical ureas.Here,we have disclosed novel and highly efficient three-component coupling reactions of organic halides,so-dium cyanate and amines enabled by nickel/photoredox dual catalysis for the preparation of unsymmetrical ureas.The reaction fea-tures simple and safe operations,broad substrate scopes,and product diversities.It 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.

Cross-couplingNickelPhotoredox catalysisThree-component reactionUreasCarbamates

Ernest Koranteng、Zhen-Cao Shu、Yi-Yin Liu、Qian Yang、Bin Shi、Qiang-Xian Wu、Fen Tan、Liang-Qiu Lu、Wen-Jing Xiao

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Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction,Ministry of Education,College of Chemistry,Central China Normal University,152 Luoyu Road,Wuhan,Hubei 430079,China

Wuhan Youji Industries Co.,Ltd,No.1 2nd Chemical Rd.,Wuhan,Hubei 430082,China

Hubei Key Laboratory of Purification and Application of Plant Anti-cancer Active Ingredients,School of Chemistry and Life Sciences,Hubei University of Education,Wuhan,Hubei 430205,China

State Key Laboratory for Oxo Synthesis and Selective Oxidation,Lanzhou Institute of Chemical Physics,Chinese Academy of Sciences,Lanzhou,Gansu 730000,China

School of Chemistry and Chemical Engineering,Henan Normal University,Xinxiang,Henan 453007,China

Wuhan Institute of Photochemistry and Technology,Wuhan,Hubei 430082,China

State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China

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国家自然科学基金国家自然科学基金国家自然科学基金国家自然科学基金国家自然科学基金国家自然科学基金湖北省自然科学基金Central China Normal University

2227111392256301218221039195620121820102003216020522022CFB413

2024

10.1002/cjoc.202300500

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子：0.848
ISSN：1001-604X
年,卷(期)：2024.42(3)
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