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

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 challenging.Herein,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 conversion.the 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

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Copper-catalyzed conjugate addition of allene-derived nucleophiles to alkenyl-substituted carboxamides

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Chinese Chemical Letters 2024年第3期35卷 239-242页

作者： Bin Fu Yue Zhao Xiuping Yuan Yanfei Li Jianjun Yin Simin Wang Tao Xiong Qian Zhang Jilin Province Key Laboratory of Organic Functional Molecular Design&Synthesis Department of ChemistryNortheast Normal UniversityChangchun 130024China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China School of Chemistry and Environmental Engineering Changchun University of Science and TechnologyChangchun 130012China

Catalytic Michael addition reaction represents a fundamental importance in organic synthetic chemistry.Whereas corresponding conversions toward intrinsically low reactive enamide remains an ongoing challenging.We herein report a copper-catalyzed conjugate addition of Allenes toβ-substituted alkenyl amides,one of the most challenging Michael acceptors.The present method utilizes readily available Allenes as the latent carbon-based nucleophiles and simple,commonβ-substituted alkenyl amides as starting materials,unlike previous methods that usually preinstall an activating group to improve the reactivity of amide or uses highly reactive stoichiometric quantities of organometallics.Hence,this approach shows good functional group compatibility and can be implemented under mild reaction conditions with excellent level of chemo-and regioselectivities.

关键词： CuH catalysis Allenes Unsaturated amide Conjugate addition Regioselectivity

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Trace amount of single-atom palladium-catalyzed selective hydrosilylation of Allenes

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Nano Research 2022年第8期15卷 7091-7098页

作者： Li-Ping Pang Xin-Yu Li Shi-Cheng Ren Hong-Min Lin Ying-Chun Wang Ying-Ming Pan Hai-Tao Tang State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources School of Chemistry and Pharmaceutical Sciences of Guangxi Normal UniversityGuilin 541004China College of Chemistry and Chemical Engineering Jishou UniversityJishou 416000China

Using fewer catalysts to promote the chemical conversion of more substrates is the dream synthesis pursued by synthetic chemists.Achieving highly selective reactions using trace amounts(Allenes(Pd loading was as low as 0.98 ppm).The synergistic effect of the dispersed catalytic active sites in the catalyst and supports with ligand regulation function can directionally realize the formation of specifically configured hydrosilylation products.The as-fabricated single-atom catalyst(SAC;i.e.,Pd1@POL-5)showed an amazing catalytic efficiency and selectivity for hydrosilylation of allene(turnover number was up to 772,358,which was 200 times higher than previously recorded,and regioselectivity>100:1).The catalyst could be recycled numerous times in a continuous flow system without reductions in activity and selectivity.This work demonstrated the application prospect of the SAC in the synthesis of complex organic compounds and trace amount catalysis,which can lay the foundation for its large-scale and industrialized application in drug synthesis and other fields.

关键词： trace catalysis single-atom catalysts hydrosilylation Allenes

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Construction of 3-Azabicyclo[3.1.0]hexane Backbone by the Reaction of Allenes with Allylamines via Tandem Michael Addition and Copper-Mediated Oxidative Carbanion Cyclization

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Chinese Journal of Chemistry 2021年第3期39卷 666-670页

作者： Hui Xu Teng Han Xiaoyan Luo Wei-Ping Deng Shanghai Key Laboratory of New Drug Design and School of Pharmacy East China University of Science and Technology130 Meilong RoadShanghai 200237China

Main observation and conclusion A facile synthetic method for the construction of 3-azabicyclo[3.1.0]hexane in the presence of copper catalyst system was developed.The reaction proceeds through Michael addition of allylamines with Allenes followed by copper-mediated intramolecular oxidative carbanion 5-exo-trig radical cyclization,affording potential biologically active 3-azabicyclo[3.1.O]hexane derivatives in moderate to high yields(42%-85%).

关键词： Oxidative coupling Allenes Allylamine 3-Azabicyclohexane Miachel addition

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Palladium-catalyzed regioselective cascade reaction of carbon dioxide,amines and Allenes for the synthesis of functionalized carbamates

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Science China Chemistry 2020年第3期63卷 331-335页

作者： Wenfang Xiong Ruixiang Cheng Bowen Wu Wanqing Wu Chaorong Qi Huanfeng Jiang Key Lab of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical EngineeringSouth China University of TechnologyGuangzhou 510640China State Key Lab of Luminescent Materials and Devices South China University of TechnologyGuangzhou 510640China

A palladium-catalyzed regioselective three-component cascade reaction of carbon dioxide,amines and Allenes has been developed,providing an expedient and practical method for the construction of a range of functionalized carbamates containing dihydrobenzofuran or indole moiety in moderate to excellent yields.The broad substrate scope,good functional group tolerance and excellent chemo-and regioselectivity are the features of the transformation.

关键词： palladium carbon dioxide three-component reaction carbamates Allenes

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