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Science China Chemistry 2019年第7期62卷 904-908页

作者： Qi Sun Linge Li Liyan Liu Yu Yang Zhenggen Zha Zhiyong Wang Hefei National Laboratory for Physical Sciences at Microscale CAS Key Laboratory of Soft Matter Chemistry & Center for Excellence in Molecular Synthesis of Chinese Academy of Sciences Collaborative Innovation Center of Suzhou Nano Science and Technology & School of Chemistry and Materials Science in University of Science and Technology of China

A copper-catalyzed 1,1-difunctionalization of terminal alkynes was achieved via a three-component reaction, providing a variety of vinyl sulfones with good yields and excellent chemo-and stereoselectivity. Preliminary mechanistic studies indicated that the reaction probably underwent a Cu-catalyzed formal C–H insertion to produce an allene intermediate, which was then trapped by a sulfonyl anion to give the corresponding product.

关键词： copper terminal alkynes germinal difunctionalization multicomponent reaction vinyl sulfones

Photoinduced difunctionalization with bifunctional reagents containing N-heteroaryl moieties

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Science China Chemistry 2023年第6期66卷 1688-1700页

作者： Wooseok Lee Inyoung Park Sungwoo Hong Department of Chemistry Korea Advanced Institute of Science and Technology(KAIST)Daejeon 34141Republic of Korea Center for Catalytic Hydrocarbon Functionalizations Institute for Basic Science(IBS)Daejeon 34141Republic of Korea

Bifunctional reagents that serve as dual coupling partners with an activating species have emerged as valuable synthetic tools in organic *** allow for the development of diverse reaction modes with enhanced efficiency and structural variability,which is in high demand for atom-economic and sustainable *** them,bifunctional reagents containing Nheteroaryl groups have received much attention due to their ability to introduce privileged N-heteroaryl moieties into complex molecules that are otherwise challenging to ***,these reagents have been employed under visible-light conditions to achieve various synthetic applications,enabling difunctionalization of alkenes,alkynes,and[1.1.1]propellanes under mild reaction conditions,providing access to highly functionalized *** this review,we provide an overview of the recent achievements and applications of photoinduced difunctionalization using bifunctional reagents containing N-heteroaryl *** systematically categorize the representative contributions in the field based on bifunctional reagents and their reactivity *** review aims to highlight the potential of these reagents as powerful synthetic tools for sustainable and diverse synthesis.

关键词： bifunctional reagents N-heteroarylation photoreaction difunctionalization radical reaction

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Electrochemical synthesis of β-hydroxy-, β-alkoxy-, and β-carbonyloxy sulfones by vicinal difunctionalization of olefins

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Chinese Chemical Letters 2019年第8期30卷 1509-1511页

作者： Zhefan Zhang Jiyao Yan Dengke Ma Jianwei Sun Shenzhen Research Institute The Hong Kong University of Science and Technology(HKUST)Shenzhen 518057China Department of Chemistry The Hong Kong University of Science and Technology(HKUST)Hong KongChina

An electrochemical vicinal heterodifunctionalization of olefins for the synthesis ofβ-oxysulfones is *** suitable choice of the conditions,including current,electrodes,and electrolyte,this oxidation reaction proceeded efficiently in an undivided cell without the use of a stoichiometric chemical *** addition to the previously established synthesis ofβ-hydroxysulfones in the presence of water,minor modification of this protocol by using either external alcohol nucleophiles or internal carboxylic acid nucleophile also led to the synthesis ofβ-alkoxysulfones,andβ-sulfonyl lactones.

关键词： Olefins difunctionalization Electrochemical synthesis Sulfones

Cobalt-Catalyzed difunctionalization of Styrenes via Ligand Relay Catalysis

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Chinese Journal of Chemistry 2023年第24期41卷 3633-3638页

作者： Bingcheng Wang Yufeng Sun Zhan Lu Department of Chemistry Zhejiang UniversityHangzhouZhejiang310058 China College of Chemistry Zhengzhou UniversityZhengzhouHenan450001 China

Here,we report a cobalt-catalyzed sequential dehydrogenative Heck silylation/hydroamination of styrenes with hydrosilane and diazo compound to access 1-amino-2-silyl compounds with excellent *** difunctionalization reaction could undergo smoothly using 1 mol%catalyst loading with good functional group *** only di-and tri-substituted hydrosilanes,but also alkoxysilane is suitable,which does explore the scope of the family of 1-amino-2-silyl *** ligand relay phenomenon between neutral tridentate NNN ligand and anionic NNN ligand is observed for the first time via absorption spectral analysis in this one-pot,two-step *** primary mechanism has been proposed based on the control experiments.

关键词： Ligand relay catalysis difunctionalization Styrene Alkoxysilane Hydroamination Diazo compounds

Recent Advances on the Electrochemical difunctionalization of Alkenes/Alkynes

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Chinese Journal of Chemistry 2019年第3期37卷 292-301页

作者： Haibo Mei Zizhen Yin Jiang Liu Hailong Sun Jianlin Han College of Chemical Engineering Nanjing Forestry UniversityNanjingJiangsu 210037China Nanjing Research Institute of Sinopec Yangzi Petrochemical Co. Ltd.NanjingJiangsu 210048China Nanjing University University of Oklahoma Texas Tech University

Electroorganic synthesis is an emerging area of high impact research in organic chemistry, which is considered as one of the green and efficient methods and attracts growing research attention. In this review, we summarized comprehensively the recent literature reports on the electrochemical oxidative difunctionalization of unsaturated C—C bonds. The reaction types described in this review included electrochemical intermolecular cyclization, electrochemical intramolecular cyclization, and electrochemical difunctionalization of alkenes/alkynes. This review focuses on the discussion of its synthetic generality for the preparation of functionalized compounds and the related electrochemical oxidative reaction mechanism.

关键词： Electrochemical difunctionalization Alkenes/Alkynes

Visible light promoted difunctionalization reactions of alkynes

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Chinese Journal of Catalysis 2019年第7期40卷 1003-1019页

作者： Xiang Ren Zhan Lu Department of Chemistry Zhejiang UniversityHangzhou 310058ZhejiangChina

Visible light promoted difunctionalization of alkynes is reviewed. The difunctionalization reaction is achieved by different reagents. Radicals such as carbon(sp3), carbon(sp2), and other heteroatom(P, S, N, Se, O, and halide) radicals initiated by visible light can undergo radical addition to a carbon-carbon triple bond. Upon further transformation, the desired difunctionalized products are obtained. Some organometallic complexes can be activated by visible light;the difunctionalization of alkynes is catalyzed by these species. Other reagents like 1,3-dipole precursors could also react with alkynes to give difunctionalization products;here, the 1,3-dipole derivatives are obtained by visible light photocatalysis. So far, the strategy has been succeeded in the formation of C–C bonds and C–X bonds. Several valuable chemical skeletons have been constructed under mild conditions. However, high regio-and stereoselectivities in some direct difunctionalization methodologies are yet to be achieved.

关键词： Visible light photocatalysis difunctionalization Cyclization Alkyne Redox catalyst

High-valent Metal catalysis in the difunctionalization of Alkenes

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High-valent Metal catalysis in the Difunctionalization of Al...

Copper-promoted domino cyanation/Ullmann coupling toward difunctionalized acenaphthylenes with various optoelectronic properties

中国化学会全国第十一届有机合成化学学术研讨会

作者： Fei Wang Haitao Zhu Jiashun Cheng Guosheng Liu Shanghai Institute of Organic Chemistry CAS

difunctionalization alkenes presents one of the most powerful methods available for the regioselective formation C-C ***,our efforts were focused on the catalytic difiinctionalization of C=C bonds utilizing transition metal,in which high-valent metal intermediate was proven to be important for the C-X bond *** found that some special chemical bonds were achieved from high-valent metal center in the presence of weak nucleophiles,such as C-F bond from fluoride ion,C-OH bond from *** addition,the final oxidative cleavage C-M bonds were demonstrated as slow *** on these observations,the more challenging intermolecular difiinctionalization of olefins was also further explored.

关键词： difunctionalization Alkenes Intermolecular reaction Transition metal High valent

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Science China Chemistry 2023年第5期66卷 1450-1456页

作者： Yang Wang Yang Hu Junfeng Guo Zongrui Wang Yang Li Fengxiang Qie Chunfeng Shi Lei Zhang Yonggang Zhen Advanced Innovation Center for Soft Matter Science and Engineering State Key Laboratory of Organic-Inorganic CompositesBeijing University of Chemical TechnologyBeijing 100029China Wuhan National Laboratory for Optoelectronics Huazhong University of Science and TechnologyWuhan 430074China State Key Laboratory of Luminescent Materials and Devices South China University of TechnologyGuangzhou 510640China Normal College Shenyang UniversityShenyang 110044China State Key Laboratory of Catalytic Materials and Reaction Engineering Research Institute of Petroleum ProcessingSINOPECBeijing 100083China

Tremendous progress has been made on aromatic fusion of acenaphthylene towards organic ***,scarce studies focus on the functionalization of acenaphthylene without resort to aromatic extension,although vinylene double bond is highly reactive ascribed to the ring strain of the fused ***,for the first time we employ copper-promoted domino cyanation/Ullmann coupling to achieve a series of difunctionalized acenaphthylene imides(ANIs)with varied optoelectronic *** Ullmann homocoupling and crosscoupling can be combined with cyanation for difunctionalization of *** introduction of cyano groups influences oppositely not only the energy levels but also the antiaromaticity of the fivemembered rings in ANIs relative to the dimethylamino substituent due to the electron donating or withdrawing *** altering the functional units,the optical and electrical characteristics have been tailored rationally;thus p,n or ambipolar semiconducting properties can be achieved for the ANI *** article opens up possibilities to the development of organic semiconducting materials based on ANIs without aromatic extension,which is promising for applications in organic electronics.

关键词： acenaphthylene difunctionalization organic semiconductors organic field-effect transistors

Recent advances in electrooxidative radical transformations of alkynes

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Science China Chemistry 2023年第3期66卷 703-724页

作者： Yan Zhang Zhenzhi Cai Svenja Warratz Chanchan Ma Lutz Ackermann Key Laboratory of the Ministry of Education for Advanced Catalysis Materials Drug Discovery&Innovation CenterCollege ofChemistry and Life SciencesZhejiang Normal UniversityJinhua 321000China Institut für Organische und Biomolekulare Chemie and Woehler Research Institute for Sustainable Chemistry(WISCh) Georg-August-Universität GöttingenGermany

During the past few years,electrochemical oxidative reactions through radical intermediates have emerged as an environmentally-benign,powerful platform for the facile formation of C–E(E=C,N,S,Se,O and Hal)bonds through singleelectron-transfer(SET)processes at the *** unsaturated molecules and unusual structural motifs can,for instance,be directly constructed under exceedingly mild reaction conditions through initial radical attack onto *** minireview highlights the recent advances in electrooxidation in radical reactions until June 2022,with a particular focus on radical additions onto alkynes.

关键词： electrosynthesis electrooxidation radicals alkynes additions difunctionalization

Catalytically generated noncovalent ammonium dienolate:a versatile platform for the development of organocatalytic asymmetric cascade reactions

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Science China Chemistry 2024年第8期67卷 2524-2546页

作者： Jun-Bing Lin Dong-Sheng Ji Peng-Fei Xu State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical EngineeringLanzhou UniversityLanzhou 730000China Shaanxi Key Laboratory of Chemical Reaction Engineering College of Chemistry and Chemical EngineeringYan’an UniversityYan’an 716000China

Organocatalytic cascade reactions represent a powerful strategy for the rapid construction of complex chiral molecules with multiple stereocenters from simple substrates under mild conditions. The intriguing structural feature and diverse reactivity of catalytically generated dienolate species render them competent and versatile intermediates for the development of practical and valuable cascade reactions. Over the past years, a plethora of innovative and pioneering noncovalent ammonium dienolatemediated cascade reactions have been designed and implemented under the catalysis of chiral organocatalysts, making dienolate activation a general, robust, and complementary method for the functionalization of unsaturated carbonyl compounds and related substances. This review illustrates the recent advances in organocatalytic noncovalent ammonium dienolate-mediated cascade reactions(mainly from 2010 to 2023), including the cascade transformations of ammonium dienolates directly generated from unsaturated ketone/aldehyde, ester/lactone/azlactone, amide/lactam/pyrazolone/oxindole, and alkylidene nitrile compounds. The contents are arranged based on the reaction types of the ammonium dienolates, with an emphasis on cascade 2,5-, 3,5-, and 4,5-difunctionalizations of these intermediates. Furthermore, other cascade reactions involving the 1,3-, 2,3-, and even more complex 3,4,5-reactivities of ammonium dienolates were also discussed. The reaction pathway, reaction stereoinduction, and synthetic applications of the ammonium dienolate-mediated cascade reactions were highlighted throughout the article. As a stimulating and ever-growing research area, the organocatalytic noncovalent ammonium dienolate-mediated cascade reactions are expected to continue demonstrating their magic power for constructing chiral targets in the future and further expanding the boundaries of asymmetric catalysis.

关键词： organocatalysis asymmetric catalysis ammonium dienolate cascade reaction difunctionalization