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学者姓名：郑梅芳
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Abstract ：
A metal-free heterogeneous protocol is established herein for the synthesis of value-added gamma-amino acid scaffolds via carbocarboxylation of alkenes with CO2 and alkylamines under visible light irradiation. The protocol shows broad substrate scope under mild reaction conditions and good stability of the catalyst for recycle tests. Moreover, the methodology could be feasible to the late-stage derivatization of several natural products, enriching the chemical arsenal for practical application.
Keyword ：
boron carbonitride boron carbonitride carbon dioxide carbon dioxide carboxylation carboxylation gamma-amino acids gamma-amino acids metal-free photocatalysis metal-free photocatalysis
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| GB/T 7714 | Wu, Ziwei , Zhai, Senmao , Luo, Meizhen et al. Metal-Free Heterogeneous Photocatalysis for Carbocarboxylation of Alkenes: Efficient Synthesis of γ-Amino Carboxylic Derivatives [J]. | CHEMISTRY-AN ASIAN JOURNAL , 2024 , 19 (5) . |
| MLA | Wu, Ziwei et al. "Metal-Free Heterogeneous Photocatalysis for Carbocarboxylation of Alkenes: Efficient Synthesis of γ-Amino Carboxylic Derivatives" . | CHEMISTRY-AN ASIAN JOURNAL 19 . 5 (2024) . |
| APA | Wu, Ziwei , Zhai, Senmao , Luo, Meizhen , Dong, Quan , Wu, Shiwen , Zheng, Meifang . Metal-Free Heterogeneous Photocatalysis for Carbocarboxylation of Alkenes: Efficient Synthesis of γ-Amino Carboxylic Derivatives . | CHEMISTRY-AN ASIAN JOURNAL , 2024 , 19 (5) . |
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A multicomponent heterogeneous semiconductor photocatalytic sulfinylsulfonylation of alkenes with alkyl iodides and SO2 was displayed under mild metal-free conditions by using boron carbonitride (BCN) as the alternative photocatalyst. This approach has resulted in the production of a wide range of structurally diverse sultine products in moderate to high yields, using readily available starting materials including alkyl iodides and olefins with broad functional group tolerance. The method is also suitable for the late-stage functionalization of complex bioactive molecules. A radical-polar crossover cyclization (RPCC) process was proposed based on mechanistic studies.
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| GB/T 7714 | Zhou, Pan , Zhang, Yongxin , Chen, Jiarong et al. Multicomponent Heterogeneous Semiconductor Photocatalytic Sulfinylsulfonylation of Alkenes with Alkyl Iodides and SO2 [J]. | ORGANIC LETTERS , 2024 , 26 (50) : 10816-10821 . |
| MLA | Zhou, Pan et al. "Multicomponent Heterogeneous Semiconductor Photocatalytic Sulfinylsulfonylation of Alkenes with Alkyl Iodides and SO2" . | ORGANIC LETTERS 26 . 50 (2024) : 10816-10821 . |
| APA | Zhou, Pan , Zhang, Yongxin , Chen, Jiarong , Yang, Xiaoxiao , Xu, Hui , Ma, Xinyue et al. Multicomponent Heterogeneous Semiconductor Photocatalytic Sulfinylsulfonylation of Alkenes with Alkyl Iodides and SO2 . | ORGANIC LETTERS , 2024 , 26 (50) , 10816-10821 . |
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Abstract ：
A photocatalytic process was developed for intermolecular reductive coupling of aliphatic ketones with alkynes/alkenes to furnish tertiary alcohols. Mechanistic studies support that boron carbonitrides (BCN) promote the single electron reduction of unactivated aliphatic ketones to generate ketyl radicals with visible light irradiation, which then react with alkynes and alkenes to afford the allylic and aliphatic alcohols, respectively. The heterogeneous photocatalytic system is compatible with diverse substrates including pharmaceutical-related molecules (43 examples) with reusability and scale-up experiments, verifying the complementary synthetic utility of this method to the homogeneous catalysts.
Keyword ：
aliphatic ketones aliphatic ketones intermolecular cross-coupling intermolecular cross-coupling ketyl radical ketyl radical tertiary alcohols tertiary alcohols
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| GB/T 7714 | Xia, Yanping , Sun, Luyang , Cheng, Jiajia et al. Intermolecular reductive coupling of aliphatic ketones with alkynes and alkenes by BCN photocatalysts [J]. | SCIENCE CHINA-CHEMISTRY , 2024 , 68 (1) : 181-185 . |
| MLA | Xia, Yanping et al. "Intermolecular reductive coupling of aliphatic ketones with alkynes and alkenes by BCN photocatalysts" . | SCIENCE CHINA-CHEMISTRY 68 . 1 (2024) : 181-185 . |
| APA | Xia, Yanping , Sun, Luyang , Cheng, Jiajia , Wang, Sibo , Zheng, Meifang , Wang, Xinchen . Intermolecular reductive coupling of aliphatic ketones with alkynes and alkenes by BCN photocatalysts . | SCIENCE CHINA-CHEMISTRY , 2024 , 68 (1) , 181-185 . |
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A visible-light-induced protocol has been developed for the construction of C(sp(2))& horbar;P bonds with heterogeneous boron carbonitrides (BCN). The system features with broad scope and mild reaction conditions, providing various aryl phosphates in moderate to good yields from arenes and aryl halides. Mechanism studies verify a radical process, and C & horbar;H bond cleavage is not involved in the rate-determined step. Furthermore, the strategy allows the late-stage phosphonation of biologically active compounds and facilitates gram-scale synthesis, which offers a metal-free arene for valuable phosphorus-containing compounds.
Keyword ：
Boron carbonitride Boron carbonitride C(sp(2))& horbar;P cross-coupling C(sp(2))& horbar;P cross-coupling Heterogeneous photocatalysis Heterogeneous photocatalysis Radical Radical Visible light Visible light
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| GB/T 7714 | Wang, Rong , Liu, Xin , Hou, Hao et al. Visible-Light-Induced C(sp2)―P Cross-Coupling Reactions Catalyzed by Boron Carbonitride [J]. | CHEMCATCHEM , 2024 , 17 (5) . |
| MLA | Wang, Rong et al. "Visible-Light-Induced C(sp2)―P Cross-Coupling Reactions Catalyzed by Boron Carbonitride" . | CHEMCATCHEM 17 . 5 (2024) . |
| APA | Wang, Rong , Liu, Xin , Hou, Hao , Zheng, Meifang . Visible-Light-Induced C(sp2)―P Cross-Coupling Reactions Catalyzed by Boron Carbonitride . | CHEMCATCHEM , 2024 , 17 (5) . |
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A visible-light-induced carboxylation of styrenes using CO2 that proceeds via a halogen-atom-transfer pathway using alkyl iodides as a promoter has been developed. Alkyl iodides, reagents that are challenging to react under photoredox conditions, and CO2 could be assembled into electron-deficient styrenes for the synthesis of aryl acetic acids. The late-stage functionalization of bioactive molecules showed the synthetic utility of the halogen-atom-transfer system.
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| GB/T 7714 | Zhai, Senmao , Wang, Rong , Dong, Quan et al. A photochemical halogen-atom-transfer pathway for the carboxylation of alkenes with CO2 [J]. | ORGANIC CHEMISTRY FRONTIERS , 2023 , 10 (19) : 4816-4820 . |
| MLA | Zhai, Senmao et al. "A photochemical halogen-atom-transfer pathway for the carboxylation of alkenes with CO2" . | ORGANIC CHEMISTRY FRONTIERS 10 . 19 (2023) : 4816-4820 . |
| APA | Zhai, Senmao , Wang, Rong , Dong, Quan , Cheng, Jiajia , Zheng, Meifang , Wang, Xinchen . A photochemical halogen-atom-transfer pathway for the carboxylation of alkenes with CO2 . | ORGANIC CHEMISTRY FRONTIERS , 2023 , 10 (19) , 4816-4820 . |
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Abstract ：
本发明公开了一种半导体光催化活化二氧化碳制备苯丙酸类衍生物的方法，其以介孔硼氮碳材料为光催化剂，在室温和常压、可见光光照条件下，实现二氧化碳的固定制备苯丙酸类衍生物。本发明将介孔硼氮碳材料用于光催化二氧化碳的固定与转化。在可见光下进行，反应操作简单，条件温和，成本低，符合实际生产需要，避免金属残留，具有极大的应用潜力。本方法较传统的二氧化碳加成反应具有更高的区域选择性、更温和的反应条件以及更强的经济适用性。
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| GB/T 7714 | 王心晨 , 郑梅芳 , 袁涛 et al. 半导体光催化活化二氧化碳制备苯丙酸类衍生物的方法 : CN202210317517.8[P]. | 2022-03-29 00:00:00 . |
| MLA | 王心晨 et al. "半导体光催化活化二氧化碳制备苯丙酸类衍生物的方法" : CN202210317517.8. | 2022-03-29 00:00:00 . |
| APA | 王心晨 , 郑梅芳 , 袁涛 , 孙鹭杨 , 吴紫微 , 吴世文 . 半导体光催化活化二氧化碳制备苯丙酸类衍生物的方法 : CN202210317517.8. | 2022-03-29 00:00:00 . |
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Abstract ：
A sustainable system for the carbocarboxylation of olefins with redox-active esters and CO(2 )via visible-light-induced photoredox catalysis has been developed using metal-free boron carbonitride (BCN) as the photocatalyst. The scheme introduces versatile alkyl groups (including primary, secondary, and tertiary) and CO2 into the C-C double bond in a fully regioselective manner to produce valuable carboxylic derivatives with excellent yields.
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| GB/T 7714 | Hou, Hao , Luo, Meizhen , Zhai, Senmao et al. Metal-free semiconductors for visible-light-induced carbocarboxylation of styrenes with aliphatic redox-active esters and CO2 [J]. | GREEN CHEMISTRY , 2023 , 26 (3) : 1317-1321 . |
| MLA | Hou, Hao et al. "Metal-free semiconductors for visible-light-induced carbocarboxylation of styrenes with aliphatic redox-active esters and CO2" . | GREEN CHEMISTRY 26 . 3 (2023) : 1317-1321 . |
| APA | Hou, Hao , Luo, Meizhen , Zhai, Senmao , Yuan, Tao , Zheng, Meifang , Wang, Sibo . Metal-free semiconductors for visible-light-induced carbocarboxylation of styrenes with aliphatic redox-active esters and CO2 . | GREEN CHEMISTRY , 2023 , 26 (3) , 1317-1321 . |
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The selective hydrogenation reactions play a key role in industrial manufacture of fine chemicals, which mainly rely on noble metal catalysts. Herein, a noble-metal-free hybrid photosystem is established, in which boron carbonitride (BCN) and nickel bis-diphosphine complex (NiP) catalyze cooperatively the semi-hydrogenation of alkynes with high efficiency and excellent selectivity (>99%) under mild reaction conditions. In the process, BCN catalyst acts as an “electronic motor” and light harvester to establish the electron- and hydrogen-atom-delivery-transport chains to molecular NiP catalyst, with the ultimate output of reduced products. The work presents a photosystem that displays great potential for further organic transformations with high selectivity via cooperative organic photosynthesis. © 2022 CCS Chemistry. All rights reserved.
Keyword ：
alkyne alkyne boron carbonitride boron carbonitride nickel bis-diphosphine complex nickel bis-diphosphine complex photocatalysis photocatalysis selective hydrogenation selective hydrogenation
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| GB/T 7714 | Yuan, T. , Huan, S. , Ge, B. et al. Semi-Hydrogenation of Alkynes by a Tandem Photoredox System Free of Noble Metal [J]. | CCS Chemistry , 2022 , 4 (8) : 2597-2603 . |
| MLA | Yuan, T. et al. "Semi-Hydrogenation of Alkynes by a Tandem Photoredox System Free of Noble Metal" . | CCS Chemistry 4 . 8 (2022) : 2597-2603 . |
| APA | Yuan, T. , Huan, S. , Ge, B. , Lin, S. , Zheng, M. , Wang, X. . Semi-Hydrogenation of Alkynes by a Tandem Photoredox System Free of Noble Metal . | CCS Chemistry , 2022 , 4 (8) , 2597-2603 . |
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The direct reduction of inert planar arenes and heteroarenes with visible light remains rarely explored, as the energy of one visible-light photon is unable to overcome the stabilization of aromatics. Here we report a system based on boron carbonitride semiconductor, which can reduce arenes and heteroarenes in water under blue light irradiation. The system features the advantage of low-cost, high-efficiency, facile separation, benign environmental profile and broad substituent tolerance. The methodology can be extended to late-stage functionalization and/or deuteration of drugs, hormones and axially chiral compounds with conserved chirality. Moreover, gram-scale synthesis is successfully implemented with catalyst recycling. Mechanistic investigations support a consecutive blue-light-induced energy and electron transfer process, which accumulates sufficient energy to reduce arenes to arene anions by absorbing two photons successively. The metal-free system introduces a simple and sustainable reactivity mode for semiconductor photocatalysts and enriches the chemical toolkit for a class of demanding and valuable organic transformations.
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| GB/T 7714 | Yuan, Tao , Sun, Luyang , Wu, Ziwei et al. Mild and metal-free Birch-type hydrogenation of (hetero)arenes with boron carbonitride in water [J]. | NATURE CATALYSIS , 2022 , 5 (12) : 1157-1168 . |
| MLA | Yuan, Tao et al. "Mild and metal-free Birch-type hydrogenation of (hetero)arenes with boron carbonitride in water" . | NATURE CATALYSIS 5 . 12 (2022) : 1157-1168 . |
| APA | Yuan, Tao , Sun, Luyang , Wu, Ziwei , Wang, Rong , Cai, Xu , Lin, Wei et al. Mild and metal-free Birch-type hydrogenation of (hetero)arenes with boron carbonitride in water . | NATURE CATALYSIS , 2022 , 5 (12) , 1157-1168 . |
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Photochemistry provides a sustainable pathway for organic transformations by inducing radical intermediates from substrates through electron transfer process. However, progress is limited by heterogeneous photocatalysts that are required to be efficient, stable, and inexpensive for long-term operation with easy recyclability and product separation. Here, we report that boron carbonitride (BCN) ceramics are such a system and can reduce organic halides, including (het)aryl and alkyl halides, with visible light irradiation. Cross-coupling of halides to afford new C-H, C-C, and C-S bonds can proceed at ambient reaction conditions. Hydrogen, (het)aryl, and sulfonyl groups were introduced into the arenes and heteroarenes at the designed positions by means of mesolytic C-X (carbon-halogen) bond cleavage in the absence of any metal-based catalysts or ligands. BCN can be used not only for half reactions, like reduction reactions with a sacrificial agent, but also redox reactions through oxidative and reductive interfacial electron transfer. The BCN photocatalyst shows tolerance to different substituents and conserved activity after five recycles. The apparent metal-free system opens new opportunities for a wide range of organic catalysts using light energy and sustainable materials, which are metal-free, inexpensive and stable.
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| GB/T 7714 | Yuan, Tao , Zheng, Meifang , Antonietti, Markus et al. Ceramic boron carbonitrides for unlocking organic halides with visible light [J]. | CHEMICAL SCIENCE , 2021 , 12 (18) : 6323-6332 . |
| MLA | Yuan, Tao et al. "Ceramic boron carbonitrides for unlocking organic halides with visible light" . | CHEMICAL SCIENCE 12 . 18 (2021) : 6323-6332 . |
| APA | Yuan, Tao , Zheng, Meifang , Antonietti, Markus , Wang, Xinchen . Ceramic boron carbonitrides for unlocking organic halides with visible light . | CHEMICAL SCIENCE , 2021 , 12 (18) , 6323-6332 . |
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