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Visible Light-Promoted Ring-Opening Alkenylation of Cyclic Hemiacetals through β-Scission of Alkoxy Radicals

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Chinese Journal of Chemistry 2023年第3期41卷 259-264页

作者： Jiang-Ling Shi Zixuan Wang Zeyu He Bowen Dou Jianbo Wang Beijing National Laboratory of Molecular Sciences(BNLMS)and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education College of ChemistryPeking UniversityBeijing100871 China The State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of Sciences354 Fenglin LuShanghai200032 China

The chemistry of alkoxy radicals was extensively explored during the period of 1960s to 1990s,but it has remained dormant for the past few decades.Recently,alkoxy radicals attract the attentions again,because new methods for generating alkoxy radical species have emerged.These newly developed methods are mainly based on the photolysis by visible light under mild conditions,thus allowing for new transformations of the carbon-centered radical species that are generated from theβ-scission or hydrogen abstraction of the alkoxy radicals.

关键词： Radical reactions Cleavage reactions Visible-light irradiation Decarboxylation Synthetic methods

Metal-Free Photocatalytic[4+2]Annulation of Acrylamides with 2-Benzyl-2-bromocarbonyls to Assemble Tetralin-1-carboxamides

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Chinese Journal of Chemistry 2024年第2期42卷 157-163页

作者： Weicai Li Lu Tan Yijun Chen Rui Liu Zhongyu Qi Shixuan Yuan Zhanwen Huang Siping Wei Xi Du Dong Yi Nuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province School of PharmacySouthwest Medical UniversityLuzhouSichuan 646000China Department of Chemistry School of Basic Medical ScienceSouthwest Medical UniversityLuzhouSichuan 646000China Department of Pharmacy Affiliated HospitalSouthwest Medical UniversityLuzhouSichuan 646000China

Tetralin-1-carboxamides are frequently incorporated in myriad medicinally important molecules.However,their existing synthetic routes not only suffer from some drawbacks such as tedious procedures,harsh reaction conditions,narrow substrate scope,low yields,and environmental problems,but are also based upon the elaboration of uneasily available non-linear tetralin derivatives.Herein,we describe a metal-and additive-free visible light-induced[4+2]annulation of two simple linear starting materials,namely acrylamides and 2-benzyl-2-bromocarbonyls,through a cascade C(sp^(3))-Br/C(sp^(2))-H bond cleavage,double C-C bond formation,and aromatization sequence.The developed protocol provides a convenient,efficient,and green approach to a variety of tetralin-1-carboxamide derivatives with good functional group compatibility.Importantly,the resulting products could also undergo the Licl-mediated mono-decarboxylative cyclization process to further furnish the architecturally novel bridged polycyclic imides with excellentcis-diastereoselectivities.

关键词： Annulation Metal-free Photoredox catalysis Tetralin-1-carboxamide Cyclic imides Synthetic methods C-C coupling Radical reactions Reaction mechanisms

Photocatalytic Transition-Metal-Free Direct 3-Acetalation of Quinoxaline-2(1H)-ones

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Chinese Journal of Chemistry 2022年第22期40卷 2655-2662页

作者： Chunhua Ma Hui Meng Jing Li Xianguang Yang Yuqin Jiang Bing Yu Collaborative Innovation Centre of Henan Provincefor Green Manufacturing of Fine Chemicals Key Laboratory of Green Chemical Media and ReactionsMinistry of EducationHenan Engineering Research Centre of Chiral Hydroxyl PharmaceuticalHenan Engineering Laboratoryof Chemical Pharmaceutical and Biomedical MaterialsSchool of Chemistry and Chemical EngineeringHenanNormal UniversityXinxiangHenan453007China Green Catalysis Centre College of ChemistryZhengzhou UniversityZhengzhouHenan 45001China

A general transition-metal-free visible-light-promoted 3-acetalation reaction of quinoxaline-2(1H)-ones was developed under mild conditions.By employing 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene(4CzIPN)as an inexpensive photocatalyst,and glyoxylic acid acetal as a radical source,various acetalated quinoxaline-2(1H)-ones were constructed in moderate to good yields.Moreover,the versatility of this protocol is highlighted by the successful application in the late-stage modification of drug molecules and the various functionality transformations.The excellent antitumor activity of the acetalated product demonstrated that this streamlined and sustainable approach could have emerged as a powerful strategy for structural modification in medicinal chemistry.

关键词： Photocatalysis Transition-metal-free Synthetic methods Radical reactions Antitumor activity

Photoredox Synthesis of Thio-Functionalized Cyclic Ethers Using N-Sulfenyl Phthalimides as a Thiyl-Radical Precursor

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Chinese Journal of Chemistry 2023年第15期41卷 1823-1828页

作者： Maojian Lu Rong-Bin Liang Can-Ming Zhu Qing-Xiao Tong Jian-Ji Zhong Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province ShantouUniversityShantouGuangdong515063China Chemistry and Chemical Engineering Guangdong Laboratory ShantouGuangdong 515031China

Comprehensive Summary A visible-light mediated exclusively regioselective synthesis of 2,2-disubstituted thio-functionalized tetrahydrofurans,tetrahydro-pyrans and oxepanes has been described through an operationally simple and mild photoredox protocol.Thiyl radical generated from N-phenylsulfenyl phthalimide by photoredox catalysis was proven to be the key reactive intermediate in this reaction.

关键词： Photoredox catalysis Cyclic ethers Thio-functionalization Thiyl radical Sulfenylating reagent N-Sulfenyl phthalimides Synthetic methods Cycloaddition Reaction mechanisms

Catalyst-Free Regio-and Diastereoselective Synthesis of Heterocyclic Nucleosides in the Eco-friendly Solvent 2-Methyltetrahydrofurant

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Chinese Journal of Chemistry 2023年第2期41卷 167-172页

作者： Xiaodong Gu Qingwei Du Weijian Song Jun(Joelle)Wang Department of Chemistry Hong Kong Baptist UniversityKowloonHong KongChina Department of Chemistry Southern University of Science and TechnologyShenzhenGuangdong 518055China

An efficient and practical synthesis of heterocyclic nucleosides is developed by a catalyst-free highly regioselective and diastereose-lective[3+2]annulation of a-purine-substituted acrylates with nitrones.The reaction operates with excellent functional group toler-ance,very mild reaction conditions,and with the green,sustainable,and eco-friendly 2-methyltetrahydrofuran(2-MeTHF)as sol-vent.Compared with other reactions of electron-deficient olefin dipolarophiles with nitrones,different regioselective cycloaddition products were observed in this work.This 1,3-dipolar cycloaddition reaction gives a series of isoxazolidinyl nucleosides in good to excellent yields with promising applications in biochemistry and medicinal chemistry.

关键词： Heterocycle Nucleoside Catalyst-free Annulation Regioselectivity Synthetic methods Cycloaddition

Palladium-Catalyzed Tandem Cyclization Strategy for the Assembly of 3-Halo-1,2,5-triarylpyrroles from N-Alkylanilines and Haloalkynes

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Chinese Journal of Chemistry 2023年第2期41卷 181-187页

作者： Songjia Fang Huanfeng Jiang Wanqing Wu Key Laboratory of Functional Molecular Engineering of Guangdong Province State Key Laboratory of Luminescent Materials and DevicesSchool of Chemistry and Chemical EngineeringSouth China University of TechnologyGuangzhouGuangdong 510640China

This report discloses a distinctive palladium-catalyzed sequential tandem cyclization reaction of two molecular haloalkynes and one molecular N-alkylanilines,leading to the efficient assembly of various 3-halo-1,2,5-triarylpyrrole derivatives.Two carbon-carbon tri-ple bonds and one carbon-halogen bond in two molecular haloalkynes are transformed conveniently in one single step,which may involve the aminoalkynylation of haloalkyne and cyclization of the newly formed enyne intermediate.The high chemo-and regiose-lectivities,good functional group tolerance and late-stage modification of the halopyrrole products further illustrate the synthetic value of this strategy.

关键词： Palladium-catalyzed Haloalkynes N-Alkylanilines Cyclization Halopyrroles Amines Insertion Synthetic methods

Visible Light-Induced C-5 Selective C-H Radical Borylation of Imidazo[1,2-a]pyridines with NHC-Boranes

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Chinese Journal of Chemistry 2023年第2期41卷 193-198页

作者： Huitao Zheng Hao Lu Chaobo Su Runlong Yang Limin Zhao Xiang Liu Hua Cao School of Chemistry and Chemical Engineering and Guangdong Cosmetics Engineering&Technology Research Center Guangdong Pharmaceutical UniversityZhongshanGuangdong 528458China

A visible-light-induced C-5 selective C-H borylation of imidazo[1,2-a]pyridines with NHC-BH3 via Minisci-type radical borylation re-action has been developed for the first time.The present sustainable protocol provides a new family of regioselectively C5-borylated imidazopyridines that would otherwise be difficult to prepare.It is a supplement to site-selective borylation of azines(nitrogen-con-taining aromatic heterocycles)and the assembly of sp2 carbon-boron bond.

关键词： Photochemistry Boron C-H activation Imidazo[12-a]pyridines Radicals Synthetic methods

Transition-Metal-Free Catalyzed Dehydrative Coupling of Quinoline and Isoquinoline N-Oxides with Propargylic Alcohols

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Chinese Journal of Chemistry 2022年第1期40卷 71-78页

作者： Zhao-Nan Cai Xiang-Xuan Feng Yuecheng Zhang Cong-Cong Lu Ya-Ping Han Jiquan Zhao School of Chemical Engineering and Technology Hebei University of TechnologyTianjin 300130China

A novel,green,and transition-metal-free protocol for the facile modification of quinoline and isoquinoline derivatives is introduced,starting from readily available and environmentally benign quinoline and isoquinoline N-oxides with propargylic alcohols in the presence of Na_(2)S_(2)O_(8) or K_(2)S_(2)O_(8) at 100℃.The one-pot transformation features the advantages of good functional group compatibility,short reaction time,operational simplicity,and highly efficient reaction system.This protocol,which produces water as the only byproduct,provides efficient and atom-economical access to a class of fascinating quinoline and isoquinoline products in satisfactory yields.The method is effective on the gram scale,thus highlighting the inherent practicality of this methodology.

关键词： Synthetic methods Alcohols Nitrogen heterocycles Transition-metal-free Solvent-free

Convenient Synthesis of Thioester-Substituted Oxindoles by Palladium-Catalyzed Thiocarbonylative Cyclization with Sulfonyl Chlorides as the Sulfur Source

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Chinese Journal of Chemistry 2023年第2期41卷 188-192页

作者： Ren-Rui Xu Xiuyu Fang Xinxin Qi Xiao-Feng Wu Department of Chemistry Key Laboratory of Surface&Interface Science of Polymer Materials of Zhejiang ProvinceZhejiang Sci-Tech UniversityHangzhouZhejiang 310018China Dalian National Laboratory for Clean Energy Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalianLiaoning 116023China Leibniz-Institut für Katalys e e.V Albert-Einstein-Straβe 29aRostock 18059Germany

A general and straightforward strategy for the synthesis of thioester-substituted oxindoles via a palladium-catalyzed thiocarbonyla-tive cyclization process has been developed.With sulfonyl chlorides as promising sulfur source,a wide range of thioester-substituted oxindoles were obtained in moderate to high yields.Both aryl and alkyl sulfonyl chlorides were well tolerated,and Mo(CO)6 played a dual role as both a CO source and a reductant in this approach.

关键词： Alkene Carbonylation Oxindoles Palladium Thiocarbonylation Sulfonyl Chlorides Synthetic methods