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Sustainable functionalization and modification of materials via multicomponent reactions in water

Frontiers of Chemical Science and Engineering 2022年第9期16卷 1318-1344页

作者： Siamak Javanbakht Tahereh Nasiriani Hassan Farhid Mohammad Taghi Nazeri Ahmad Shaabani Department of Organic Chemistry Shahid Beheshti UniversityTehran ***Iran Рeoples’Friendship University of Russia(RUDN University) Moscow 117198Russian Federation

In materials chemistry,green chemistry has established firm ground providing essential design criteria to develop advanced tools for efficient functionalization and modification of materials.Particularly,the combination of multicomponent reactions in water and aqueous media with materials chemistry unlocks a new sustainable way for constructing multi-functionalized structures with unique features,playing significant roles in the plethora of applications.multicomponent reactions have received significant consideration from the community of material chemistry because of their great efficiency,simple operations,intrinsic molecular diversity,and an atom and a pot economy.Also,by rational design of multicomponent reactions in water and aqueous media,the performance of some multicomponent reactions could be enhanced by the contributing“natural”form of water-soluble materials,the exclusive solvating features of water,and simple separating and recovering materials.To date,there is no exclusive review to report the sustainable functionalization and modification of materials in water.This critical review highlights the utility of various kinds of multicomponent reactions in water and aqueous media as green methods for functionalization and modification of siliceous,magnetic,and carbonaceous materials,oligosaccharides,polysaccharides,peptides,proteins,and synthetic polymers.The detailed discussion of synthetic procedures,properties,and related applicability of each functionalized/modified material is fully deliberated in this review.

关键词： materials multicomponent reactions modification functionalization water

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multicomponent reactions for Diverse Synthesis of N-Substituted and NH 1,4-Dihydropyridines

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Chinese Journal of Chemistry 2014年第3期32卷 219-226页

作者： Jieping Wan Youyi Zhou Yunyun Liu Zheng Fang Chengping Wen Key Laboratory of Functional Small Organic Molecule Ministry of Educationand College of Chemistry and Chemical EngineeringJiangxi Normal UniversityNanchangJiangxi 330022China College of Basic Medical Sciences Zhejiang Chinese Medical UniversityHangzhouZhejiang 310053China

The multicomponent reactions of aldehydes,electron deficient alkynes and amines have been successfully per-formed to yield a number of symmetrical 2,6-unsubstituted 1,4-dihydropyridines(1,4-DHPs).This method has been found generally applicable for the synthesis of both N-substituted and N-unsubstituted 1,4-DHPs by employing secondary amine to activate the alkyne component via enaminoester intermediates.The present method runs through an enamine type activation,which is different from the known approach employing AcOH as solvent.

关键词： multicomponent reactions enamine activation enaminoester 1,4-dihydropyridine diversity

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One-Pot Stereoselective Synthesis of Different Fused Multicyclic Iminosugars Based on the Iminium-lon Intermediate

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Chinese Journal of Chemistry 2024年第2期42卷 142-150页

作者： Song Xie Jilai Wu Likai Zhou Chao Wei Xiaoliu Li Hua Chen Key Laboratoryof Chemical Biology of Hebei Province College of Chemistry and Material ScienceHebei UniversityBaodingHebei 071002China College of Chemistry and Chemical Engineering Xingtai UniversityXingtaiHebei 054001China

Different novel fused multicyclic iminosugars were synthesized from D-ribose tosylate,aniline and vinyl ethyl ether by one-pot three-component stereoselective[4+2]reaction at different temperatures.The iminium-ion is the key intermediate for the reaction.As a result,several complex fused iminosugars 3a were obtained by aza-Diels-Alder mechanism at 60℃,while a series of aza-C-glycosides 5a were prepared by Mannich reaction at room temperature accompanied by another tetrahydroquinoline-fused iminosugars 4a(tricyclic derivatives)through aza-Diels-Alder cycloaddition.This strategy will help to construct structurally diverse and bioactive iminosugar analogues.

关键词： Fused multicyclic iminosugar Aza-Diels-Alder cycloaddition Mannich reaction Tetrahydroquinoline multicomponent reactions Enantioselectivity Cyclization

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Recent advances in visible light-mediated chemical transformations of enaminones

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Chinese Chemical Letters 2024年第2期35卷 4-15页

作者： Yu Han Liyun Zhou Chengyu Wang Shangti Feng Rong Ma Jie-Ping Wan College of Chemistry and Chemical Engineering Jiangxi Normal UniversityNanchang 330022China School of Chemistry and Chemical Engineering Linyi UniversityLinyi 276000China Linyi Sanfeng Chemical Co. Ltd.Linyi 276000China

Enaminones,which possesses both the nucleophilic enamine as well as electrophilic enone structures,are well known versatile building blocks in organic synthesis.Meanwhile,visible light-mediated reactions have emerged as useful synthetic strategy with enhanced sustainability.Around the last decade,various photochemical transformations of enaminones have been developed to construct cyclic or acyclic compounds.In this review,we describe the recent advances in visible light-mediated chemical transformations of enaminones.Detailed discussion on the reaction mechanism of the related reactions is given to provide guide to the reader.Finally,a summary on the existing challenges and the future outlook towards the development of practical photocatalytic reactions of enaminones is also presented.

关键词： Enaminone Visible light C-H functionalization C=C bond cleavage Cyclization multicomponent reactions

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Synthesis of biheteroaryls via 2-methyl quinoline C(sp^(3))-H functionalization under metal-free conditions

Green Synthesis and Catalysis

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Green Synthesis and Catalysis 2024年第1期5卷 73-76页

作者： Dahan Wang Yuhan Yang Fuhong Xiao Jinbing Liu Guojiang Mao Guo-Jun Deng Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education Hunan Province Key Laboratory of Green Organic Synthesis and ApplicationCollege of ChemistryXiangtan UniversityXiangtan 411105China Department of Food and Chemical Engineering Shaoyang UniversityShaoyang 422100China School of Chemistry and Chemical Engineering Henan Normal UniversityXinxiang 453007China

An acetic acid-promoted C(sp^(3))-H functionalization of 2-methyl quinoline,enaminoesters and elemental sulfur for the synthesis of 3,4,5-trisubstituted isothiazoles under metal-free conditions has been developed.This approach provides viable access to various 5-(quinolin-2-yl)isothiazoles in moderate to good yields with good functional group tolerance.Moreover,the success of the gram-scale reaction gives this reaction a great potential application.

关键词： C(sp^(3))-H functionalization multicomponent reactions Biheteroaryls Elemental sulfur Metal-free

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An Environmentally Benign Catalytic Method for Versatile Synthesis of 1,4-Dihydropyridines via multicomponent reactions

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中国化学:英文版 2015年第5期33卷 568-572页

作者： Shuo Cao Shanshan Zhong Changfeng Hu Jie-Ping Wan Chengping Wen Key Laboratory of Functional Small Organic Molecule Ministry of EducationCollege of Chemistry and Chemical EngineeringJiangxi Normal UniversityNanchangJiangxi 330022China College of Basic Medical Sciences Zhejiang Chinese Medical UniversityHangzhouZhejiang 310053China

The synthesis of diverse 1,4-dihydropyridines have been achieved via the multicomponent reactions of aldehydes,enaminones and amines.The reactions have been smoothly performed in water to provide all products with mod... 详细信息

关键词： lactic acid catalysis multicomponent reactions 1 4-dihydropyridines green catalysis heterocycle

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Multifunctional Polymer-Protein Conjugates Generated by multicomponent reactions

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Chinese Journal of Chemistry 2021年第8期39卷 2287-2295页

作者： Tengfei Mao Chongyu Zhu Lei Tao State Key Laboratory of NBC Protection for Civilian Beijing 102205China The Key Laboratory of Bioorganic Phosphorus Chemistry&Chemical Biology(Ministry of Education) Department of ChemistryTsinghua UniversityBeijing 100084China Department of Materials Science Fudan UniversityShanghai 200433China

Recently,multifunctional polymers for protein conjugation have been facilely synthesized through the multicomponent reactions(MCRs).In this mini-review,current progress in the generation of multifuncti onal polymers with protei n-reactive groups via MCRs is summarized.These mult functional polymers react with model therapeutic proteins,forming multifunctional polymer-protein conjugates,which are prototypes of sophisticated theranostic agents and antibacterial vaccine candidates.In comparison with the traditional multi-step synthesis,the preparation of multifunctional polymers for protein conjugation through MCRs is straightforward and convenient.Due to these properties,MCRs have the potential to become a new general strategy to achieve polymer-protein conjugates for biological and medical applications.

关键词： Protein modifications Conjugation Poly(ethylene glycol)(PEG) multicomponent reactions Polymers

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multicomponent reactions for the Synthesis of Imidazo[1,2-a ]pyridines via Pd/Cu Catalysis

Multicomponent Reactions for the Synthesis of Imidazo[1,2-a ...

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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： Li Xianwei Huo Yanping School of Chemical Engineering and Light Industry Guangdong University of Technology

By virtue of their inherent convergence and high productivity,together with their exploratory and complexity-generating power,MCRs have naturally become a rapidly evolving field of research and have attracted the attention of both academic and industrial scientists.Imidazo[1,2-a]pyridines,which represent an important class of natural products,pharmaceuticals,and bioactive compounds,were intensively synthesized based on 2-aminopyridines through condensation or/and oxidative coupling of the C-N bond.Thus,the development of rapid synthetic methods to assembly highly functionalized imidazo[1,2-a]pyridines is desirable for pharmaceutical field.Herein,we have demonstrated Pd/Cu catalyzed multicomponent reactions for the rapid synthesis of imidazo[1,2-a]pyridines starting from aminopyridine,terminal alkynes,alkyl bromides with molecular oxygen or silicon.Notably,the obtained products could be readily undergoes further modifications,which possess the potential for the modular synthesis of imidazo[1,2-a]pyridine derivatives.

关键词： multicomponent reactions Highly Functionalized Hetercycles Modular Synthesis

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An Olefinic 1,2-α-Boryl Migration Enables 1,2-Bis(boronic esters)via Radical-Polar Crossover Reaction

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Chinese Journal of Chemistry 2022年第5期40卷 582-588页

作者： Feng Zhang Shangteng Liao Lu Zhou Kai Yang Chenglan Wang Yixian Lou Cece Wang Qiuling Song Key Laboratory of Molecule Synthesis and Function Discovery Fujian Province UniversityCollege of ChemistryCollege of Materials Sciences Engineering at Fuzhou UniversityFuzhouFujian350108 China Institute of Next Generation Matter Transformation College of Materials Science Engineering at Huaqiao University668 Jimei BoulevardXiamenFujian361021 China

A radical-induced 1,2-α-boryl migration through radical polar crossover reactions has been described.In this work,in situ formed vinyldiboron“ate”complexes from alkenyl Grignard reagent and diborylalkanes react with commercial radical precursors under light initiation.This three-component process enables diborylation of alkene.This protocol features high atom economy,a broad substrate scope as well as good functional group toleration with mild conditions.

关键词： Borates Radical reactions 1,2-αBoryl migration multicomponent reactions Diborylation

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Pd-catalyzed diastereoselective 1,1-diarylation of 1,1-disubstituted alkenes enabling the modular synthesis of 1,1,2,2-tetraarylethanes

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Science China Chemistry 2023年第12期66卷 3539-3545页

作者： Chengxi Zhang Yang Xi Jingping Qu Yifeng Chen Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Feringa Nobel Prize Scientist Joint Research CenterFrontiers Science Center for Materiobiology and Dynamic ChemistrySchool of Chemistry and Molecular EngineeringEast China University of Science&TechnologyShanghai 200237China

The highly diastereoselective dicarbofunctionalization of substituted olefins still remains a daunting challenge in synthetic chemistry.Herein,we report a Pd-catalyzed diastereoselective 1,1-diarylation of 1,1-diarylethylene with chelation group free to enable the modular synthesis of smart material candidates,1,1,2,2-tetraarylethanes(TAEs),which represent the first protocol by assembling four different aryl groups into ethane motif.Preliminary mechanistic experiments suggest that the crucial Pd–H species generated in situ do not disengage from the alkene intermediate during the reaction.

关键词： 1,1,2,2-tetraarylethane palladium cross-coupling reaction alkene multicomponent reactions

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