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Copper-catalyzed direct oxidation and N-arylation of benzylamines with diaryliodonium salts

Science China Chemistry 2014年第8期57卷 1132-1136页

作者： LIU Xin MAO Dan WU ShengYing YU JianJun HONG Gang ZHAO Qiao WANG LiMin Key Laboratory for Advanced Materials and Institute of Fine Chemicals East China University of Science and Technology

An efficient approach for the synthesis of N-arylated amides was developed via copper(Ⅱ) triflate-catalyzed direct oxidation of(aryl)methylamines to primary arylamides by air and subsequent N-arylation by diaryliodonium salts. Various substituted benzylamines could be applied in the reaction, providing a series of N-arylated amides in moderate to good yields. This method showed convenient, practical, and environment friendly advantages.

关键词： copper(Ⅱ) triflate diaryliodonium salts N-arylated amides oxidation

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Concise synthesis of xanthones by the tandem etherification——Acylation of diaryliodonium salts with salicylates

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Chinese Chemical Letters 2018年第6期29卷 985-988页

作者： Gaoxiaozheng Liu Chao Wu Bifeng Chen Ru He Chao Chen MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology Department of Chemistry Tsinghua University The Graduate School at Shenzhen Tsinghua University

An efficient synthetic method for multi-substituted xanthones was developed. The reaction of diaryliodonium salts and salicylates was employed for the preparation of the xanthones. This method proceeded through an intermolecular etherification-acylation to give target heterocycles in good yields（up to 91%）. Multi-substituted xanthones were gained by shifting the substituent of salicylates or diaryliodonium salts

关键词： Xanthone diaryliodonium salts Etherification Acylaion Multiple substituent

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Efficient synthesis of cyclic imides by the tandem N-arylation-acylation and rearrangement reaction of cyanoesters with diaryliodonium salts

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Chinese Chemical Letters 2023年第5期34卷 281-285页

作者： Zhiyuan Bao Chao Chen MOE Key Laboratory of Bioorganic Phosphorus Chemistry&Chemical Biology Department of ChemistryTsinghua UniversityBeijing 100084China

Available online An efficient method for the synthesis of multi-substituted cyclic imides was developed with cyanoesters and diaryliodonium *** method proceeds through a cascade of N-arylationacylation and rearrangement to give target heterocycles in good yields(up to 99%).This method has the major advantages of a broad substrate scope,excellent functional group *** strategy was also extended to the fused cyclic imides,such as malonimides,succinimides and glutarimides.

关键词： Cyclic imides Cyanoesters diaryliodonium salts N-Arylation-acylation Rearrangement

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Diarylation of Heterocycle Aromatics with diaryliodonium salts Catalyzed by Transition Metals

Diarylation of Heterocycle Aromatics with Diaryliodonium Sal...

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中国化学会·第十五届全国有机合成化学学术研讨会

作者： Zheng Xu Rui Wang 杜正银 College of Chemistry and Chemical Engineering Northwest Normal University 西北师范大学

diaryliodonium salts have attracted much attention in organic synthesis in recent years due to their easily preparation and good stability to humidity and air. The unique T-type structure of diaryliodonium salts makes them having highly electron-deficient nature and good leaving-group ability of iodobenzene, which results in the excellent electronphilic arylation *** diaryliodonium salts can easily react with various nucleophiles to form arylating products. We used thiazoles and oxazoles as nucleophiles, the diarylation reaction of thiazoles and oxazoles using diaryliodonium salts as arylating reagents is firstly *** reaction was catalyzed by transition metals in the presence of a ***, the diarylation of thiophenes catalyzed by TM under similar reaction conditions was ***, an efficient atom-economic one-step process for the preparation of 2,5-diarylthiazoles and 2,5-diaryloxazoles from thiazoles, oxazoles and diaryliodonium salts is *** reaction was conducted in a one-pot *** above diarylation protocols have some advantages, such as step-economy, simple operation, high efficiency, wide scope of substrates and excellent group tolerance.

关键词： Diarylation diaryliodonium salts Csp2-H activation Cross coupling Heterocyclic aromatics Transition metal catalysis Atom-economic reaction

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Base-Promoted Coupling of Carbon Dioxide,Amines and diaryliodonium salts:A Phosgene-Free Route to Arvl Carbamates

Base-Promoted Coupling of Carbon Dioxide,Amines and Diarylio...

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中国化学会全国第十二届有机合成化学学术研讨会

作者： Wenfang Xiong Chaorong Qi Youbin Peng Tianzuo Guo Min Zhang Huanfeng Jiang School of Chemistry and Chemical Engineering South China University of Technology

The conversion of carbon dioxide(CO

关键词： diaryliodonium salts Carbon Dioxide Aryl Carbamates

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Copper-Catalyzed Annulation of Isothiocyanates with diaryliodonium salts: Arylation–Cyclization Approach to Quinolines

Copper-Catalyzed Annulation of Isothiocyanates with Diarylio...

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中国化学会全国第十二届有机合成化学学术研讨会

作者： Wang,Yuan-Chao Guo,Wei-Si Wen,Li-Rong College of Chemistry and Molecular Engineering Qingdao University of Science and Technology

Quinolines are privileged scaffolds in various bioactive natural products and pharmaceuticals.1 Therefore,many methods for the synthesis of quinolines have been developed including Combes quinoline synthesis,Friedlander synthesis,Skraup synthesis and so *** on our previous studies on the diaryliodonium salts,we herein reported a novel copper-catalyze tandem arylation-cyclization process for the preparation of quinolines from readily available isothiocyanates with diaryliodonium salts.

关键词： quinolines isothiocyanate diaryliodonium salts

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Cu-catalyzed Deacylation Arylation of 1H-1,2,3-Benzotriazoles

Cu-catalyzed Deacylation Arylation of 1H-1,2,3-Benzotriazole...

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中国化学会·第十五届全国有机合成化学学术研讨会

作者： Wenying Zhang Yangyang Wang 杜正银 College of Chemistry and Chemical Engineering Northwest Normal University 西北师范大学

Benzotriazole can be found in some bioactive molecules as a nitrogen-containing *** of their interesting structure, high reactivity, and anticancer activity, N-substituted benzotriazoles are widely used in synthetic organic chemistry, materials science, and pharmaceuticals. In the past two decades, hypervalent, λ-iodane organic compounds have been efficiently utilized as successful reagents in organic chemistry. diaryliodonium salts were used widely in organic synthesis because of their low toxicity, stability, high reactivity, and ***, diaryliodonium salts are particularly important among the quickly growing number of aryliodonium compounds because they afford efficient arylation of diverse nucleophiles, in particular heteroatom *** the other hand,recent applications of diaryluodonium salts have focused on metal-catalyzed arylation reaction under mild *** years, our group achieved the Pd-catalyzed C-H arylation of benzothiazoles and triazoles with diaryliodonium salts to prepare 2-arylbenzothiazoles and 5-aryltriazoles. We reported herein a cheap metal catalysed N-deacylation and thereafter N-arylation of N-acetylbenzothiazoles with diaryliodonium *** reaction was proceeded regioselectively to form N1-arylbenzotriazoles in good to excellent yield under mild conditions.

关键词： Deacylation Arylation diaryliodonium salts 1-H-1,2,3-Benzotriazoles Transition Metal Catalysis

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Pd-catalyzed C-H Arylation for the Synthesis of 2-Arylbenzothiazoles

Pd-catalyzed C-H Arylation for the Synthesis of 2-Arylbenzot...

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中国化学会第十三届全国有机合成化学学术研讨会

作者： Rui Wang Yang Che Zhengyin Du College of Chemistry and Chemical Engineering Northwest Normal University

Substituted benzothiazole derivatives are a class of important compounds in organic synthesis and pharmaceutical *** can be effectively used for the building blocks of anticancer,1 antitumor,2 anti-inflammatory,3 anti-HCV,4 antioxidant and anti-glutamic acid drug molecules.5 So more efficient and fast synthesis of 2-arylbenzothiazole compounds in recent years has been paid much attention by synthetic *** recent years,diaryliodonium（III） salts（Ar2 IX） are receiving increasing attention of scientists and research groups around the world as a versatile arylating reagents,owing to their favorable safety profile,ease of handling,and air and moisture stability.6 In 2014,Kumar et al7 reported a Cu-catalyzed C-H arylation of azaheterocycles with diaryliodonium salts which involved the coupling of ***,the scope of substrate was only limited to benzothiazole and the effect of substituents were not *** our continuous investigation on palladium catalyzed C-H activation functionalization of phenyl substituted heterocyclic aromatics8 and considering the wide application of 2-arylbenzothiazoles,we herein report an efficient palladium-catalyzed direct C-H arylation reaction of benzothiazoles with diaryliodonium salts as arylating reagents to form 2-arylbenzothiazole *** summary,a novel,simple and direct arylation of benzothiazoles with diaryliodonium salts to form 2-arylbenzothiazoles has been *** cross-coupling reaction is catalyzed by palladium bromide in the presence of cesium carbonate and phosphorus *** protocol has a wide substrate scope and well group tolerance to give the desired products in moderate to high yields.

关键词： benzothiazoles arylation diaryliodonium salts cross coupling C-H activation

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Copper-Catalyzed Arylation-Cyclization of o-Alkynylphenyl Isothiocyanates to Generate Functional Quinolin-4（1H）-ones

Copper-Catalyzed Arylation-Cyclization of o-Alkynylphenyl Is...

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中国化学会全国第十二届有机合成化学学术研讨会

作者： Shen,Qiang-Yu Guo,Wei-Si Wen,Li-Rong College of Chemistry and Molecular Engineering Qingdao University of Science and Technology

diaryliodonium salts are environmentally benign regeants and widely used in the construction of arylated ***,we developed a new copper-catalyzed tandem arylation-cyclization process for the synthesis of quinolin-4（1H... 详细信息

关键词： quinolin-4(1H)-ones isothiocyanate diaryliodonium salts

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