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Electrochemical Radical borylation of Aryl Iodides

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Chinese Journal of Chemistry 2019年第4期37卷 347-351,I0002页

作者： Junting Hong Qianyi Liu Feng Li Guangcan Bai Guoquan Liu Man Li Onkar S.Nayal Xuefeng Fu Fanyang Mo Department of Energy and Resources Engineering College of EngineeringPeking UniversityBeijing 100871China State Key Laboratory of Natural and Biomimetic Drugs School of Pharmaceutical SciencesPeking UniversityBeijing 100871China Department of Biomedical Engineering College of EngineeringPeking UniversityBeijing 100871China Jiangsu Donghai Silicon Industry S&T Innovation Center Jiangsu Weiming Environmental Protection S&T Co.Ltd.No.38Guangming RdDonghai CountyJiangsu 222300China

Herein,we report the first electrochemical strategy for the borylation of aryl iodides via a radical pathway using current as a driving force.A mild reaction condition allows an assorted range of readily available aryl iodides to be proficiently converted into synthetically valuable arylboronic esters under transition metal catalyst-free ***,this method also shows good functional group *** control mechanistic experiments reveal the formation of aryl radical as a key intermediate and the current plays an important role in the generation of radical intermediate.

关键词： Electrochemical Radical borylation Aryl Iodides proficiently converted

Synergistic Pd/Cu-catalyzed regio-and stereoselective cascade Heck cyclization/borylation/cross-coupling

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Chinese Chemical Letters 2023年第12期34卷 166-171页

作者： Yifan Wang Yuanyuan Ping Wangqing Kong The Institute for Advanced Studies(IAS) Wuhan University.Wuhan 430072China

A cooperative Pd/Cu-catalyzed three-component cross-coupling reaction of alkynes,B_(2)Pin_(2) and alkene-tethered aryl halides is *** reaction proceeds under mild conditions and shows broad sub-strate scope,providing a variety of heterocycles containing tetrasubstituted alkenylboronate moieties in synthetically useful yields with excellent chemoselectivity and *** transformation fea-tures the catalytic generation ofβ-borylalkenylcopper intermediates and their use in Pd-catalyzed Heck cyclization/*** enantioselective cascade cyclization/cross-coupling process has also been developed for the synthesis of enantiomerically enriched oxindole bearing a tetrasubstituted alkenyl-boronate moiety.

关键词： Palladium/copper catalysis Heck cyclization Alkene difunctionalization Cross-coupling borylation

Heterogeneous photocatalytic borylation of aryl iodides mediated by isoreticular 2D covalent organic frameworks

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Chinese Chemical Letters 2023年第5期34卷 594-597页

作者： Pengna Shang Xiaoli Yan Yang Li Junji Liu Guang Zhang Long Chen Department of Chemistry and Tianjin Key Laboratory of Molecular Optoelectronic Science Tianjin UniversityTianjin 300072China State Key Laboratory of Supramolecular Structure and Materials College of ChemistryJilin UniversityChangchun 130012China

Metal-free heterogeneous photocatalysts provide an environmental-friendly and cost-efficient avenue for green organic *** organic frameworks(COFs)as heterogeneous photocatalysts showcase promising potential in the field of photocatalytic organic reactions due to their high porosity,insolubility and tailor-made ***,thus far,COF-based catalysts only mediated a few types of ***,we developed a series of isoreticular nitrogen-rich covalent organic frameworks(N-COFs)with comparable porous structures as photocatalysts which effectively mediated the borylation of aryl iodides with broad substrate ***,6N-COF exhibits excellent photocatalytic efficiency and superior *** suggests a new pathway to construct efficient heterogeneous photocatalysts for the borylation of aryl halides.

关键词： Covalent organic frameworks Nitrogen-rich Heterogeneous photocatalysis borylation Green organic synthesis

Electrochemically promoted decarboxylative borylation of alkyl N-hydroxyphthalimide esters

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Chinese Chemical Letters 2022年第3期33卷 1555-1558页

作者： Jian-Jun Dai Xin-Xin Teng Wen Fang Jun Xu Hua-Jian Xu School of Food and Biological Engineering Hefei University of TechnologyHefei 230009China Anhui Province Key Laboratory of Advance Catalytic Materials and Reaction Engineering Hefei University of TechnologyHefei 230009China

An electrochemically promoted decarboxylative borylation reaction is reported. The reaction proceeds under mild conditions in an undivided cell without use of transition metal-or photo-catalysts. The key feature of the reaction is the compatibility of diboron reagents with the electrochemical conditions. This reaction exhibits broad substrate scope, good functional group tolerability, and easy scalability.

关键词： Electrochemical Decarboxylation borylation Alkyl boronic esters Redox active esters

Iron-Catalyzed borylation and Silylation of Unactivated Tertiary,Secondary,and Primary Alkyl Chlorides

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CCS Chemistry 2021年第9期3卷 2164-2173页

作者： Siyu Wang Minghui Sun Huan Zhang Juan Zhang Yun He Zhang Feng Chongqing Key Laboratory of Natural Product Synthesis and Drug Research School of Pharmaceutical SciencesChongqing UniversityChongqing 401331 Sichuan Key Laboratory of Medical Imaging Department of ChemistrySchool of Preclinical MedicineNorth Sichuan Medical CollegeSichuan 637000

Herein,we describe an iron-catalyzed borylation and silylation of unactivated alkyl chlorides,delivering the tertiary,secondary,and primary alkylboronic esters,and secondary,primary alkylsilanes with high *** protocol exhibits broad substrate scope and good functional group compatibility,allowing the efficient late-stage borylation of biorelevant compounds,thus offering an excellent platform in drug discovery and *** mechanistic studies suggest that an alkyl radical was involved in this catalytic system.

关键词： iron catalysis borylation silylation unactivated alkyl chlorides

Access to Stereodefined Multifunctionalizedβ,γ-Unsaturated Ketones via Chemo,Regio-and Diastereoselective Copper-Catalyzed Diborylation of Cross-Conjugated Enynones

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Chinese Journal of Chemistry 2021年第3期39卷 590-596页

作者： Shuai Zhang Xinhua Duan Pengfei Li Frontier Institute of Science and Technology Xi'an Jiaotong UniversityXi'anShaanxi 710054China School of Chemistry Xi'an Jiaotong UniversityXi'anShaanxi 710049China State Key Laboratory of Elemento-Organic Chemistry Nankai UniversityTianjin 300071China Xi'an Key Laboratory of Sustainable Energy Materials Chemistry Xi'an Jiaotong UniversityXi'anShaanxi 710049China

Main observation and conclusion Stereodefinedβ,γ-unsaturated carbony|compounds are important yet synthetically challenging units in natural products and *** herein is a mild,rapid copper-catalyzed diborylation reaction of cross-conjugated enynones as a step-economic and modular approach to stereodefined multifunctionalizedβ,γ-unsaturated ketones by fine control of chemo-,regio-,Z/E and *** substrate scope was examined and a possible catalytic cycle was proposed to explain the multifaceted selectivity.

关键词： Stereoselectivity β,γ-Unsaturated ketones Copper catalysis borylation Cross-conjugated enynones

Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes

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Chinese Chemical Letters 2024年第5期35卷 141-144页

作者： Wujun Jian Mong-Feng Chiou Yajun Li Hongli Bao Song Yang National Key Laboratory of Green Pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationCenter for R&D of Fine Chemicals of Guizhou UniversityGuiyang 550025China Strait Institute of Flexible Electronics(SIFE Future Technologies)Fujian Normal UniversityFuzhou 350117China Key Laboratory of Coal to Ethylene Glycol and Its Related Technology State Key Laboratory of Structural ChemistryFujian Institute of Research on the Structure of MatterUniversity of Chinese Academy of SciencesFuzhou 350002China

borylation of 1,3-enynes with bis(boronate)compounds often ends up with the formation of hydroborylated products,leaving the diborylation of 1,3-enynes for the formation of 1,4-diborylated allenes to be ***,a copper-catalyzed chemo-,regio-,and stereo-selective diborylation of 1,3-enynes for the efficient construction of 1,4-diborylated allenes under base-free conditions was reported.A wide range of 1,3-enynes bearing various functional groups can participant in the reaction and afforded the corresponding 1,4-diborylated allenes in good to excellent yields,which was enabled by the protocol of Bpin to BF3K *** borylcopper species was supposed to selectively attack the C-C triple bond of the 1,3-enynes.

关键词： Copper catalysis Regioselective 1,3-Enynes borylation Allenes

Chlorine Atom Transfer of Unactivated Alkyl Chlorides Enabled by Zirconocene and Photoredox Catalysis

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Precision Chemistry 2023年第2期1卷 112-118页

作者： Toshimasa Okita Kazuhiro Aida Keisuke Tanaka Eisuke Ota Junichiro Yamaguchi Department of Applied Chemistry Waseda UniversityShinjukuTokyo 162-0041Japan

Alkyl chlorides are robust precursors to carbon radicals;however,their relative inertness has hampered their practical *** modern photochemical strategies have greatly enhanced the utility of alkyl chlorides as radical precursors,these methods often depend on strongly reducing conditions leading to unproductive side ***,we report a catalytic radical generation from 1°,2°,and 3°unactivated alkyl chlorides with zirconocene and photoredox catalysis,which enables both hydrogenation and borylation on a range of structurally complex *** mild zirconocene-catalyzed protocol shows that zirconium can render the C−Cl bond cleavage more exergonic and can lower the activation energy of the transition state,amplifying the ability of metallocenes toward halogen atom transfer.

关键词： Zirconocene Alkyl chloride Halogen atom transfer borylation Photoredox catalysis

Synthesis,Structures,and Chiroptical Properties of NBN-Doped Helicenes with Boron Atoms in the Inner Rims

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Precision Chemistry 2024年第1期2卷 28-39页

作者： Weiwen Zhuang Yujian Liu Ziqi Deng Yu Guo Philip C.Y.Chow David Lee Phillips Wei Jiang Zhaohui Wang Junzhi Liu State Key Laboratory of Synthetic Chemistry HKU-CAS Joint Laboratory on New Materials and Department of ChemistryThe University of Hong KongPokfulamHong KongChina Key Laboratory of Organic Optoelectronics and Molecular Engineering Department of ChemistryTsinghua UniversityBeijing 100084China Department of Mechanical Engineering The University of Hong KongPokfulamHong KongChina

The precise synthesis of helicenes with topologically defined length and specific heteroatomic perturbation in the screw-like conjugated skeletons plays an emerging role in the manipulation of chiral ***,selective,and programmable routes to helicenes or heterohelicenes are highly desirable yet challenging for structure-chiroptical property relationship ***,we report the synthesis and characterization of NBN-doped helicenes with boron atoms in the inner rims,enabled by the highly regioselective one-pot borylation of rationally designed precursors with,namely,fold-in or pan-out *** incorporation of nonbonded boron and nitrogen atoms resulted in narrow-band emission and improved optical properties for the single-stranded carbon *** addition,numbers and arrangement modes of fused six-membered rings have distinct effects on configurational stability and chiroptical properties,revealing that BN-[6]H with strong circular dichroism is a promising candidate for chiral *** combination of experimental and theoretical studies on these helical structures might provide insights into the design of helically chiral small-molecule-based sensors or emitters.

关键词： Nitrogen-boron Helicenes borylation Chiroptical properties Narrow-band emission