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Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade

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Chinese Chemical Letters 2024年第6期35卷 331-336页

作者： Jing-Qi Tao Shuai Liu Tian-Yu Zhang Hong xin Xu Yang xin-hua duan Li-Na Guo Department of Chemistry School of ChemistryXi’an Key Laboratory of Sustainable Energy Material Chemistry and Engineering Research Center of Energy Storage Materials and DevicesMinistry of EducationXi’an Jiaotong UniversityXi’an 710049China School of Electrical Engineering Xi’an Jiaotong UniversityXi’an 710049China State Key Laboratory of Applied Organic Chemistry Lanzhou UniversityLanzhou 730000China

A photoinduced copper-catalyzed alkoxyl triggered C-C bond cleavage/aminocarbonylation cascade is *** adjusting the structure of alkoxyl radical precursors,functionalized lactones and ketoamides were synthesized with good yields and excellent functional group tolerance under redox-neutral ***,this protocol enables the integration of lactone fragments with many amine drugs and drug fragments.

关键词： Copper catalysis Ring-expansion Aminocarbonylatioin Macrolactones Keto-amides

Photoredox catalytic alkylarylation of alkynes with arylsulfonylacetate as bifunctional reagent

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Science China Chemistry 2024年第6期67卷 2022-2028页

作者： Chonglong He Min Wang Yulong Wang Lirong Zhao Youkang Zhou Keyuan Zhang Shenyu Shen Yaqiong Su xin-hua duan Le Liu School of Chemistry Engineering Research Center of Energy Storage Materials and DevicesMinistry of EducationXi’an Key Laboratory of Sustainable Energy Material ChemistryXi’an Jiaotong UniversityXi’an710049China

Difunctionalization of alkynes represents a powerful and straightforward approach to the synthesis of complex ***,the radical difunctionalization of alkynes mediated by bifunctional reagents remains challenging and underexplored,despite significant progress having been made in alkene ***,we report a novel arylsulfonylacetate skeleton in which aryl rings are attached to acetates through SO_(2),serving as a powerful bifunctional reagent for the alkylarylation of alkynes via vinyl-radical intermediate under photoredox *** modular bifunctional reagent enables the simultaneous incorporation of a wide range of functional groups,including(hetero)aryl ring and alkyl carboxylate into alkynes,resulting in synthetically valuable all-carbon tetrasubstituted alkene *** transformation is distinguished by its redox-neutral nature,readily accessible starting materials,compatibility with diverse functional groups and its capacity to facilitate convergent *** utility of this approach was further demonstrated by the late-stage functionalization of complex molecules and the preparation of fluorescent molecules and anti-cancer drugs.

关键词： bifunctional reagent photoredox catalysis Smiles rearrangement alkylarylation tetrasubstituted acyclic all-carbon olefins

Lone pair-π interaction induced regioselective sulfonation of ethers under light irradiation

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Green Synthesis and Catalysis

Green Synthesis and Catalysis 2024年第2期5卷 117-121页

作者： Chonglong He Min Wang Bowu Dong Yaqiong Su xin-hua duan Le Liu School of Chemistry Engineering Research Center of Energy Storage Materials and DevicesMinistry of EducationXi'an Key Laboratory of Sustainable Energy Material ChemistryXi’an Jiaotong UniversityXi’an 710049China

Non-covalent interactions are of significance in supramolecular chemistry and biochemistry,while synthetic procedures driven by these weak interactions remain challenging and *** by the lone pair-π interaction presence in the Z-DNA structure,a light-induced regioselective sulfonation of ethers taking advantage of the lone pair-π interaction between the oxygen of ethers and sulfonyl chlorides has been ***,this strategy is also applicable to the sulfonation of aniline *** of the methods include readily accessible starting materials,high atom-economy,green and photocatalyst-free conditions and broad functional group *** studies suggest that the lone pair-πinteraction plays an important role to initiate the transformation.

关键词： Non-covalent interactions Lone-pair-πinteractions Sulfonyl radical Photocatalysis Ethers

Pentacoordinate Phosphoranes as Versatile Reagents in Fluoroalkylation Reactions

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CCS Chemistry 2024年第1期6卷 165-176页

作者： huanhuan Song Weihao Li Xiaoying Wang Kaiteng Wang Jingwen Li Shuai Liu Pin Gao xin-hua duan Jinbo Hu Mingyou Hu School of Chemistry Engineering Research Center of Energy Storage Materials and DevicesMinistry of EducationXi’an Key Laboratory of Sustainable Energy Material ChemistryXi’an Jiaotong UniversityXi’an 710049 Key Laboratory of Organofluorine Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032

A general method for the synthesis of bench-stable bis(difluoromethyl)pentacoordinate phosphoranes has been *** reaction is rapid,operationally simple,and easily *** pentacoordinate phosphoranes can generate both difluoromethyl radical(·CF_(2)H)and difluorocarbene(:CF_(2))***,a variety of fluoroalkylation transformations havebeen achieved by·CF_(2)H,such asoxidativedifluoromethylation of electron-deficient heterocycles,nickel/photoredox dual-catalyzed difluoromethylation of aryl bromides,and photoredox difluoromethylation of alkenes,or by:CF_(2),such as gem-difluorocyclopropanation of alkenes,base-promoted difluoromethylation of heteroatom nucleophiles,Pd-catalyzed difluoromethylation of arylboronic acids,and Cu-mediated trifluoromethylation of aryl iodides(via:CF_(2) and recombined CF_(3)-).These fluoroalkylation methods have been successfully applied to late-stage fluoroalkylation of drugs and drug-like molecules.

关键词： pentacoordinate phosphorane difluoromethyl radical difluorocarbene difluoromethylation fluoroalkylation

Regioselective C-C bond cleavage/aminocarbonylation cascade under copper catalysis

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Science China Chemistry 2024年

作者： Qi-Chao Shan Yan Zhao Yong Wu Hong-Fei Liu xin-hua duan Li-Na Guo Department of Chemistry School of Chemistry Energy Research Center of Energy Storage Materials and Devices Ministry of EducationXi'an Jiaotong University State Key Laboratory of Applied Organic Chemistry Lanzhou University

A regioselective C-C bond cleavage/aminocarbonylation cascade is presented. In recent years, tremendous progress has been made in the alkoxyl radical-mediated C-C bond cleavage of unstrained monocarbocycles. In contrast, the deconstruction and functionalization of bicyclic skeletons has been less developed and has mainly focused on the ring expansion process. Inspired by the aromatization-driven C-C bond cleavage, here we demonstrate a ring-opening/aminocarbonylation cascade under copper catalysis, in which the formation of a stable γ-lactam or succinimide skeleton reverses the selectivity of C-C cleavage. Remarkably, the photo and thermal assistance is not required when the succinimide skeleton is formed during the ring opening process. DFT calculations revealed that this unexpected ring-opening process is thermodynamically and kinetically favourable.

关键词： C-C bond cleavage controllable regioselectivity aminocarbonylation bicyclic alkoxy radical

Metal-Free Oxidative Decarboxylative Acylation/RingExpansion of Vinylcyclobutanols with a-Keto Acids by Visible Light Photoredox Catalysis

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Chinese Journal of Chemistry 2017年第3期35卷 311-315页

作者： Jin-Jiang Zhang Yuan-Bo Cheng xin-hua duan Department of Chemistry School of Science and MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter Xi' an Jiaotong University Xi'an Shaannxi 710049 China

A metal‐free visible‐light‐mediated decarboxylative acylation/ring expansion of vinylcyclobutanols with α ‐keto acids has been developed. Hypervalent iodine reagent was found to be important for promoting decarboxylation of α ‐keto acids in this tandem radical process. This protocol has been successfully applied to synthesis of a variety of substituted 1,4‐dicarbonyl compounds and tolerated some functional groups well.

关键词： visible light oxidative decarboxylation radical α‐keto acids

Oxidative thiocyanation of allylic alcohols:an easy access to allylic thiocyanates with K_(2)S_(2)O_(8) and NH_(4)SCN

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Organic Chemistry Frontiers 2022年第4期9卷 966-972页

作者： Keyuan Zhang Tianbing Liang Yulong Wang Chonglong He Mingyou Hu xin-hua duan Le Liu School of Chemistry Xi’an Key Laboratory of Sustainable Energy Materials ChemistryMOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed MatterXi’an Jiaotong UniversityXi’an 710049China

A practical method for the synthesis of allylic thioacyanates from allylic alcohols was disclosed employing K_(2)S_(2)O_(8) as the oxidant and NH_(4)SCN as the thiocyanate *** introducing a leaving group in advance,a series of disubstituted and monosubstituted allylic thiocyanate compounds were obtained in moderate to good *** transition metal-free method features mild reaction conditions,broad sub-strate scope and operational *** potential application of this method was demonstrated by some derivatization reactions of the product and mechanistic investigation indicated that a radical process is involved.

关键词： alcohols simplicity substituted

Water-promoted regio-selective trifluoromethylation of vinyl conjugated diazoacetates

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Organic Chemistry Frontiers 2022年第1期9卷 204-209页

作者： xinxin Han xin Liu Yueyun Bao Hunahuan Song Yu-Rou Zhao Xiaoying Wang Junjie Zhang Le Liu xin-hua duan Jinbo Hu Mingyou Hu School of Chemistry Xi’an Key Laboratory of Sustainable Energy Material Chemistryand MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed MatterXi’an Jiaotong UniversityXi’an 710049China Key Laboratory of Organofluorine Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032China

An efficient trifluoromethylation reaction of vinyldiazoacetates under mild reaction conditions was ***-generated CuCF_(3) was used as a trifluoromethylation reagent and water acted as both a promoter and proton *** reaction is compatible with a broad scope of functional groups and easy to *** wide functional group tolerance of the reaction enables further synthetic manipulation of the products.

关键词： products vinyl conjugated

Carbon dots-derived three-dimensional-ordered macroporous host with high penetrability and catalytic activity for LSBs under lean electrolyte

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Rare Metals 2024年第6期43卷 2560-2573页

作者： Jiao-Zi duan hua-Yu Pei Quan Yang Xue Li xin Ba Xue Yong Jun-Ling Guo Si-Yu Lu Green Catalysis Center College of ChemistryZhengzhou UniversityZhengzhou 450001China Country State Center for International Cooperation On Designer Low-Carbon&Environmental Materials School of Materials Science and EngineeringZhengzhou UniversityZhengzhou 450001China Hubei Institute of Quality Supervision Inspection Wuhan 430061China Department of Chemistry University of SheffieldSheffeld S37HFUK

The practical energy density of lithium-sulfur batteries(LSBs)is seriously limited by the high electrolyte-to-sulfur ratios(E/S).The E/S can be reduced by employing hosts with easy-to-infiltrate structure that ensures the uniform distribution of a lean electrolyte and high catalytic activity that can suppress"shuttle effect"via accelerating the slow conversion of soluble poly sulfides to insoluble *** the easy-to-infiltrate structures,the three-dimensional-ordered macroporous(3DOM)structure is easier to scale preparation and more suitable for the existing industrial ***,it is difficult to obtain the 3DOM with(1)high penetrability due to the high viscosity of frequently-used organic polymer precursors and(2)high catalytic activity due to the low confinement effect,meaning that uniformly dispersed small-sized catalytic materials are difficult to load on ***,using carbon dots(CDs)with both organic and inorganic properties as a precursor and aggregation limiting agent,a 3DOM host with high penetrability and homodispersed Ni particles of small sizes(Ni-CDs-3DOM)was *** this host:(1)CDs precursor with suitable viscosity can improve the penetrability.(2)CDs can effectively inhibit the agglomeration of Ni particles.(3)Uniformly dispersed small-size Ni particles offer high-efficiency catalytic activity toward sulfur ***,the Ni-CDs-3DOM/sulfur cathode exhibits high sulfur utilization and stable cycling performance even under high sulfur loading(5.5 mg·cm^(-2))and low E/S(6.5μl·mg^(-1)).This work indicates the usefulness of CDs in constructing hosts for LSBs with high energy density.

关键词： Lithium-sulfur batteries Carbon dots Catalytic action Easy-to-infiltrate structure Lean electrolyte