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Palladium-Catalyzed three-component Coupling Reaction of Allyl Carboxylates, Norbornenes and Diboronates InvoIving Sequential Olefins Insertion and Borylation Reaction

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Chinese Journal of Chemistry 2019年第2期37卷 140-147页

作者： Zun Li Jia Zheng Chunsheng Li Wanqing Wu Huanfeng Jiang Key Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical EngineeringSouth China University of TechnologyGuangzhouGuangdong 510640China

Summary of main observation and conclusion An efficient Pd-catalyzed three-component coupling reaction of allyl carboxylates, norbornenes and diboronates is described, which allows efficient assembly of C(sp3)-C(sp3) and C(sp3)-B bonds in a single process. Moreover, this approach shows advantages of good chemo- and regioselectivity, as well as good substrates suitability.

关键词： Palladium-Catalyzed three-component Coupling Reaction Allyl Carboxylates

Copper-catalyzed three-component reaction of imidazo[1,2-a]pyridine with elemental sulfur and arylboronic acid to produce sulfenylimidazo[1,2-a]pyridines

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Chinese Chemical Letters 2018年第9期29卷 1363-1366页

作者： Genhua Xiao Hao Min Zhilei Zheng Guobo Deng Yun Liang National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research Ministry of Education Key Laboratory of the Assembly and Application of Organic Functional Molecules College of Chemistry and Chemical Engineering Hunan Normal University

In this work, an efficient copper-catalyzed three-component reaction for the synthesis of sulfenylimidazo [1,2-a]pyridines using elemental sulfur as the sulfenylating agents has been developed. The reaction could proceed smoothly with a high degree of functional group tolerance and provide the desired products in moderate to good yield.

关键词： Copper three-component Pyridine Sulfur Arylboronic acids

An efficient three-component domino synthesis of difluoromethyl-containing 1,4-dihydropyridines under solvent and catalyst free conditions

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Science China Chemistry 2010年第7期53卷 1509-1513页

作者： LI Hui YU JinLong CAO Song SHEN Li WU MingXi CHENG JianHang QIAN XuHong Shanghai Key Laboratory of Chemical Biology Center of Fluorine Chemical TechnologySchool of PharmacyEast China University of Science and TechnologyShanghai 200237China

The difluoromethyl-containing Hantzsch 1,4-dihydropyridines were synthesized in good yields by a one-pot cyclocondensation of ethyl difluoroacetoacetate (EDFAA),a variety of aromatic aldehydes and ammonium acetate under solvent and catalyst free *** comparison of reaction conditions and products was made among the different 1,3-carbonyl substrates (ethyl acetoacetate,ethyl difluoroacetoacetate and ethyl trifluoroacetoacetate) for the Hantzsch reaction.

关键词： three-component difluoromethyl 1,4-dihydropyridines ethyl difluoroacetoacetate

three-component Coupling Catalyzed by Phosphine: Preparation of α-Amino γ-Oxo Acid Derivatives

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International Journal of Organic Chemistry 2012年第2期2卷 111-116页

作者： Yohei Oe Takeshi Inoue Hiroaki Kishimoto Mitsuhiro Sasaki Tetsuo Ohta Isao Furukawa Department of Biomedical Information Faculty of Life and Medical Sciences Doshisha University Kyotanabe Kyoto 610-0394 Japan Department of Biomedical Information Faculty of Life and Medical Sciences Doshisha University Kyotanabe Kyoto 610-0394 Japan Department of Molecular Science and Technology Faculty of Engineering Doshisha University Kyotanabe Kyoto 610-0394 Japan Department of Molecular Science and Technology Faculty of Engineering Doshisha University Kyotanabe Kyoto 610-0394 Japan

The three-component coupling reaction of ethyl propiolate (1), phthalimide (2), and aldehyde (3) catalyzed by tripheny- lphosphine, was developed. A solution of an equivalent amount of 1 and 2 in benzaldehyde (3a) in the presence of 30 mol% of PPh3 was heated at 100?C for 48 h to give N-(1-ethoxycarbonyl-3-oxo-3-phenylpropyl)phthalimide (4a) in 83% yield. This reaction was thought to proceed via vinylphosphonium salt formed from the reaction of ethyl propiolate (1) with triphenylphosphine in situ.

关键词： three-component Coupling Phosphine 2-Amino-4-Oxocarboxylic Acid

Mechanistic insight into the high stereoselectivity of Co(Ⅲ)-catalyzed three-component C-H addition cascade

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Mechanistic insight into the high stereoselectivity of Co(Ⅲ...

Cu-Catalyzed three-component One-Pot Synthesis of Aryl Sulfide with Sulfur Powder under Aqueous Conditions

第十三届全国量子化学会议

作者： Xuexiang Ma Jianbiao Liu Fang Huang Chuanzhi Sun Dezhan Chen College of Chemistry Chemical Engineering and Materials ScienceCollaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of ShandongShandong Normal University

A three-component C(sp)-H bond addition across alkene and polarized π-bonds with high stereoselectivity was reported for which CpCo catalysis was shown to be much more effective than CpRh. The reaction demonstrated excellent group tolerance to afford products in good yields and high diastereoselectivity. Herein we carried out a detailed theoretical mechanistic study for the reation to elucidate the high stereoselectivity and great difference between CpRh and CpCo catalysis in both reactivity and stereoselectivity. The results show that the whole catalytic cycle, including C(sp)-H activation, insertion of alkene, isomerization, intermolecular aldol reaction and protodemetalation. The high stereoselectivity of the products depend on the cobalt enolate addition to the ald ehyde.

关键词： high stereoselectivity three-component C-H functionalization

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Cu-Catalyzed Three-Component One-Pot Synthesis of Aryl Sulfi...

Cascade reaction of 3-formylchromones:Highly selective synthesis of 4-oxo-3-(1H-pyrrol-3-yl)-4H-chromenes

中国化学会第十三届全国有机合成化学学术研讨会

作者： Xiao Fu-Hong Chen Shu-Qing Deng Guo-Jun Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education College of ChemistryXiangtan University

Aryl sulfides are ubiquitous structural motifs found in numerous pharmaceutically active compounds and medicinally important natural ***,a variety of methods for the C-S bond construction to synthesize aryl sulfides have been developed.A typical method is based on inorganic sulfur reagents,in which sulfur powder（S8）,which is abundant and smell-free in nature,has been extensively investigated for introducing sulfur atoms into organic molecules.[1] In recent years,the transition metal-catalyzed direct sulfenylation of C-H bond using inorganic sulfur as the sulfur source has attracted considerable interest,since this strategy provides a more atom-economic route to construct the C-S bond by omitting substrate ***,we and others have developed various approaches for C-H sulfuration using sulfur powder as sulfur source,[2] whereas most of the procedures described above were carried out in organic *** the perspective of green chemistry,water is a desirable reaction medium because of its inexpensive,nontoxic and *** our continuing efforts using water as an ideal solvent for the C-H sulfenylation,[3] herein,we disclose a novel and environmentally-friendly protocol for the synthesis of aryl sulfides via C-H bond functionalization of arenes with iodohydrocarbon and sulfur powder under aqueous conditions.

关键词： Cu-catalyzed sulfur powder three-component water

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Green Synthesis and Catalysis

Green Synthesis and Catalysis 2024年第2期5卷 94-101页

作者： Ying Lv Li Chen Xinghan Yun Kun Li Shengjiao Yan Key Laboratory of Medicinal Chemistry for Natural Resource(Yunnan University) Ministry of EducationSchool of Chemical Science and TechnologyYunnan UniversityKunming 650091China

A novel method for the preparation of highly functionalized 4-oxo-3-(1H-pyrrol-3-yl)-4H-chromenes(OPCMs)from 3-formylchromones andα-isocyanoacetates via an unprecedented three-component[1+1+3]cycloaddition reaction in one pot was *** three-component cascade reaction was enabled by refluxing a mixture of the substrates in 1,4-dioxane in the presence of Ag_(2)CO_(3) as a Lewis acid *** a result,a series of functionalized pyrroles(OPCMs,3),was prepared regioselectively and in high yields(80%-88%)through the formation of three *** protocol can be used in the synthesis of OPCMs rather than through conventional,multi-step reactions and is suitable for both combinatorial and parallel syntheses of pyrroles.

关键词： 4-Oxo-3-(1H-pyrrol-3-yl)-4H-chromenes three-component Cascade reaction [1+1+3]cycloaddition 3-Formylchromones

Copper-Catalyzed [3 + 2 + 1] Cycloaddition of Alkenes with Benzoquinones and Dicarbonyl Compounds via Tandem Oxidative Dicarbofunctionalization/Cyclization Sequence

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Chinese Journal of Chemistry 2022年第14期40卷 1681-1686,I0002页

作者： Tianxing Du Song Li Yunfei He Huan Long Xigong Liu Hai-Bei Li Lei Liu School of Chemistry and Chemical Engineering Shandong University JinanShandong 250100China School of Ocean Shandong UniversityWeihaiShandong 264209China

Developed is an efficient three-component [3 + 2 + 1] cycloaddition of simple alkenes with two C—H substrates via oxidative dicarbofunctionalization/cyclization sequence. The copper-catalyzed reaction involves the formation of two C—C bonds and one C—O bond through the cleavage of three C—H bonds in a single operation. The method has an excellent functional group tolerance, and features a broad substrate scope, affording a variety of functionalized chromenes in good yields.

关键词： Alkene dicarbofunctionalization Cyclization three-component C-H Activation Oxidation

Cul-Catalyzed Multicomponent Synthesis of Aminoindolizines from Aldehydes, Amines, and Alkynes under Solvent-Free Conditions

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Chinese Journal of Chemistry 2013年第6期31卷 799-804页

作者： Changming Pan Jianping Zou Runsheng Zeng Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry Chemical Engineering and Mate- rials Science of Soochow University Suzhou Jiangsu 215123 China

A direct and efficient approach to 1-aminoindolizines through three-component one-pot reaction of heteroaryl aldehydes, secondary amines and terminal alkynes catalyzed by CuI under solvent-free conditions has been dev... 详细信息

关键词： three-component one-pot solvent-free CuI heteroaryl aldehydes