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phosphine-Catalyzed [4+3] Annulation Reaction of Indole Derivatives with MBH Carbonates:A Facile Access to Indole-1,2-fused 1,4-Diazepinones and Azepines

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Chinese Journal of Chemistry 2024年第3期42卷 271-275页

作者： Yannan Zhu Haoran Jiang Yi-Ning Wang Faculty of Chemistry and Chemical Engineering Yancheng Institute of TechnologyYanchengJiangsu224051 China

A phosphine-catalyzed [4+3] annulation between dinucleophilic indole derivatives and Morita−Baylis−Hillman (MBH) carbonates was discovered by using the N1 and N4′/C4′ nucleophilicities of the indole precursors,in which indoles act as four atom synthons. This protocol provides an efficient and facile access to indole-1,2-fused 1,4-diazepinones and azepines in good to high yields in one step,which illustrates potential synthetic utilities in drug discovery.

关键词： phosphine catalysis [4+3]Annulation Indole derivatives Nitrogen heterocycles Organocatalysis

Light-induced phosphine-catalyzed asymmetric functionalization of benzylic C–H bonds

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Science China Chemistry 2023年第1期66卷 127-132页

作者： Jiami Guo Zi-An Shen Xueting Zhou Lei Dai Yixin Lu Joint School of National University of Singapore and Tianjin University International Campus of Tianjin University Binhai New CityFuzhou 350207China Department of Chemistry National University of SingaporeSingapore 117543Singapore

Despite rapid development in the past two decades,there are still some unsolved synthetic challenges in the field of phosphine catalysis.In this report,through photo-induced activation of ortho-alkyl aromatic ketones,we achieved highly enantioselective functionalization of substrates bearing a benzylic C–H bond.In the presence of amino acid-derived bifunctional phosphine catalysts,a range of benzylic allylation products were obtained in good yields and with excellent enantioselectivities.The strategy disclosed herein offers new insight into the activation and functionalization of pronucleophiles containing less acidic C–H bonds in the domain of phosphine catalysis and beyond.

关键词： phosphine catalysis nucleophilc catalysis enantioselective benzylic C-H bonds

Asymmetric Dearomatization of Electron-Deficient Heteroarenes by a phosphine-Catalyzed[3+2]Annulation with Vinylcyclopropanes

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CCS Chemistry 2023年第9期5卷 2023-2032页

作者： Xuan Dai Fuhao Zhang Lei Dai Yixin Lu Department of Chemistry National University of SingaporeSingapore 117543 School of Chemical Engineering Nanjing University of Science and TechnologyNanjing 210094

Asymmetric dearomatization reactions of various electron-deficient heteroarenes,including benzofurans,benzothiophenes,and indoles,have been described.Through a phosphine-catalyzed[3+2]annulation with vinylcyclopropanes,readily available heteroarene feedstocks undergo smooth dearomatization reactions,delivering a diverse array of valuable chiral cyclopentabenzodihydrofuran and cyclopentaindoline scaffolds in a highly diastero-and enantioselective manner.Notably,the employment of cyclopropanes in phosphine-mediated annulation for the dearomatization of electron-deficient arenes is unknown.

关键词： dearomatization enantioselectivity phosphine catalysis electron-deficient heteroarenes vinylcyclopropanes

Catalytic chemodivergent annulations betweenα-diketones and alkynylα-diketones

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Science China Chemistry 2021年第6期64卷 991-998页

作者： Xiangwen Kong Fang Yu Zhizhou Chen Fan Gong Shuang Yang Jinggong Liu Benlong Luo Xinqiang Fang State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of MatterUniversity of Chinese Academy of SciencesFuzhou 350100China Key Laboratory of Coal to Ethylene Glycol and Its Related Technology Center for Excellence in Molecular SynthesisFujian Institute of Research on the Structure of MatterUniversity of Chinese Academy of SciencesFuzhou 350100China Orthopedics Department Guangdong Provincial Hospital of Traditional Chinese MedicineThe Second Affiliated Hospital of Guangzhou University of Chinese MedicineGuangzhou 510120China Pingxiang University Pingxiang 337055China

Four types of unprecedented and chemodivergent reactions betweenα-diketones and alkynylα-diketones have been achieved under the catalysis of phosphine and Br?nsted base,respectively,leading to the rapid construction of four different classes of biologically important but synthetically challenging molecular scaffolds including 2-hydroxyfuran-3(2H)-ones,4-hydroxy-2-oxabicyclo[2.2.1]heptan-3-ones,1,3-diaryl cyclobutanes,and 4-(furan-2(3H)-ylidene)cyclopent-2-enones.The formation of the products includes two novel rearrangement processes,and further transformations on the products can be easily achieved to deliver value-added substances such as highly functionalized cyclopentanes.Moreover,the 2-hydroxyfuran-3(2H)-one products display promising photophysical properties such as green luminescence under UV light and aggregation-induced emission effect,showing the practical application value of this work.The great potential ofα-diketones in both synthetic chemistry and material science has been unambiguously demonstrated.

关键词： chemodivergent reaction cascade annulation phosphine catalysis rearrangement reaction fluorescent material

Facile Synthesis of Spirooxindole-Cyclohexenes via phosphine-Catalyzed [4-1-2] Annulation of α-Substituted Allenoates

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Chinese Journal of Chemistry 2017年第9期35卷 1469-1473页

作者： Rongshun Chen Xia Fan Zhaozhong Xu Zhengjie He Jiangsu Key Laboratory of Pesticide Science College of Sciences Nanjing Agricultural University Nanjing Jiangsu 210095 China College of Food Science and Technology Nanjing Agricultural University Nanjing Jiangsu 210095 China The State Key Laboratory of Elemento-Organic Chemistry and Department of Chemistry Nankai University Tianjin 300071 China

A phosphine-catalyzed [4＋2] annulation of a-substituted allenoate with exocyclic alkene moiety of oxindoles or indan-1,3-diones has been developed. Thus, under the catalysis of PPh3 （20 mol%）, a series of spirooxindole- or spiroindan-1,3-dione-cyclohexenes have been obtained in moderate to excellent yields and regioselectivity from the annulations of a-methyl allenoates with 3-methyleneoxindoles or 2-methyleneindan-1,3-diones. This method offers an easy access to structurally novel spirocyclohexenes.

关键词： [4＋2] annulation reaction phosphine catalysis spirocyclohexenes allenoates synthesis

phosphine-Catalyzed Annulations between Modified Allylic Derivatives and Polar Dienes and Substituent Effect on the Annulation Mode

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Chinese Journal of Chemistry 2013年第10期31卷 1348-1351页

作者： Junjun Tian Haiyun Sun Rong Zhou Zhengjie He State Key Laboratory of Elemento-Organic Chemistry Synergetic Innovation Center of Chemical Science and Engineering ( Tianjin) and Department of Chemistry Nankai Universi~ Tianjin 300071 China

in this work, the phosphine-catalyzed annulation reactions between modified allylic derivatives and polar 1,1-dicyano-1,3-dienes have been studied. In the catalysis of PPh3 （20 mol%）, a [4 ＋ 1 ] annulation reaction is realized between a series of l,l-dicyano-2,4-diaryl-1,3-dienes and ethoxycarbonyl-activated allylic acetate, producing polysubstituted cyclopentenes in modest to excellent yields. It is also observed that the substituents of both 1,3-dienes and allylic derivatives have a significant influence on the annulation mode： under the catalysis of PPh3 or PBu3 （20 mol%）, regioselective [3 ＋ 2] annulation products are formed from differently substituted substratcs.

关键词： [4＋ 1 ] annulation reaction [3 ＋2] annulation reaction phosphine catalysis cyclopentenes dienes