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学者姓名：徐春发
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Abstract ：
N-glycosides exhibit diverse biological and pharmacological activities, making their efficient synthesis crucial for both biological research and drug development. Traditional acid-promoted N-glycosylation methods, which rely on the formation of oxocarbenium intermediates, often face significant challenges. These methods are water-sensitive and typically require neighboring group participation to achieve high selectivity. Furthermore, they depend on acid activation, rendering them incompatible with alkyl amine. Additionally, low-nucleophilicity amides often need to be converted into their TMS-derivatives to enhance reactivity, limiting the direct use of such substrates. In contrast, radical-based strategies have emerged as a promising alternative, addressing many of these limitations and leading to notable advances in N-glycosylation. This review explores the unique properties of N-glycosides, the inherent challenges of traditional N-glycosylation techniques, and the transformative advantages offered by radical-based approaches. Specifically, it highlights recent advancements in radical-mediated N-glycosylation, including photoredox radical strategies, radical/ionic hybrid approaches, and metallaphotoredox catalysis, accompanied by a detailed discussion of the underlying mechanisms. Finally, the ongoing challenges and potential future directions of N-glycoside synthesis using radical strategies are presented.
Keyword ：
Glycosyl radical Glycosyl radical N-glycosides N-glycosides N-glycosylation N-glycosylation Photocatalysis Photocatalysis Radical reactions Radical reactions
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| GB/T 7714 | Xu, Chunfa , Zhang, Qinshuo , Yusupu, Yimuran . Radical Strategy Towards N-glycosides: Current Advances and Future Prospects [J]. | CHEMBIOCHEM , 2025 , 26 (5) . |
| MLA | Xu, Chunfa 等. "Radical Strategy Towards N-glycosides: Current Advances and Future Prospects" . | CHEMBIOCHEM 26 . 5 (2025) . |
| APA | Xu, Chunfa , Zhang, Qinshuo , Yusupu, Yimuran . Radical Strategy Towards N-glycosides: Current Advances and Future Prospects . | CHEMBIOCHEM , 2025 , 26 (5) . |
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Abstract ：
Glycosyl aryl sulfones exhibit diverse biological activities. Herein, we developed a copper-promoted coupling strategy using glycosyl sodium sulfinates and aryl iodides or bromides, enabling efficient synthesis of carbohydrate-based sulfone with broad functional group compatibility. This method offers a versatile approach for the late-stage modification of bioactive molecules.
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| GB/T 7714 | Wang, Linyitian , Guo, Huize , Luo, Jiaxin et al. Copper-promoted late-stage glycosylsulfonylation of aryl iodide and bromide to access glycosyl aryl sulfones [J]. | ORGANIC & BIOMOLECULAR CHEMISTRY , 2025 . |
| MLA | Wang, Linyitian et al. "Copper-promoted late-stage glycosylsulfonylation of aryl iodide and bromide to access glycosyl aryl sulfones" . | ORGANIC & BIOMOLECULAR CHEMISTRY (2025) . |
| APA | Wang, Linyitian , Guo, Huize , Luo, Jiaxin , Zhen, Wenxu , Wang, Shiping , Xie, Zailai et al. Copper-promoted late-stage glycosylsulfonylation of aryl iodide and bromide to access glycosyl aryl sulfones . | ORGANIC & BIOMOLECULAR CHEMISTRY , 2025 . |
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Abstract ：
Previous N-glycosylation approaches have predominately involved acidic conditions, facing challenges of low stereoselectivity and limited scope. Herein, we introduce a radical activation strategy that enables versatile and stereoselective N-glycosylation using readily accessible glycosyl sulfinate donors under basic conditions and exhibits exceptional tolerance towards various N-aglycones containing alkyl, aryl, heteroaryl and nucleobase functionalities. Preliminary mechanistic studies indicate a pivotal role of iodide, which orchestrates the formation of a glycosyl radical from the glycosyl sulfinate and subsequent generation of the key intermediate, a configurationally well-defined glycosyl iodide, which is subsequently attacked by an N-aglycone in a stereospecific SN2 manner to give the desired N-glycosides. An alternative route involving the coupling of a glycosyl radical and a nitrogen-centered radical is also proposed, affording the exclusive 1,2-trans product. This novel approach promises to broaden the synthetic landscape of N-glycosides, offering a powerful tool for the construction of complex glycosidic structures under mild conditions. © 2024 Wiley-VCH GmbH.
Keyword ：
glycosyl iodides glycosyl iodides glycosyl sulfinates glycosyl sulfinates N-glycosides N-glycosides N-glycosylation N-glycosylation radical reactions radical reactions
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| GB/T 7714 | Ding, W. , Chen, X. , Sun, Z. et al. A Radical Activation Strategy for Versatile and Stereoselective N-Glycosylation [J]. | Angewandte Chemie - International Edition , 2024 , 63 (36) . |
| MLA | Ding, W. et al. "A Radical Activation Strategy for Versatile and Stereoselective N-Glycosylation" . | Angewandte Chemie - International Edition 63 . 36 (2024) . |
| APA | Ding, W. , Chen, X. , Sun, Z. , Luo, J. , Wang, S. , Lu, Q. et al. A Radical Activation Strategy for Versatile and Stereoselective N-Glycosylation . | Angewandte Chemie - International Edition , 2024 , 63 (36) . |
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A stereoselective pyridinium hexafluorophosphate-catalyzed C-glycosylation of indole is presented, featuring the plausible formation of a catalyst-acceptor complex and a crucial H-bond between the N-H group of indole and the oxygen atom at the C6 position of the glycosyl donor, which are proposed to collectively facilitate the glycosylation process. This reaction proceeds under mild conditions, enabling the selective synthesis of a wide range of C-indolyl glycosides.
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| GB/T 7714 | Xie, Lihuang , Liu, Wenchao , Guo, Zhenbo et al. A stereoselective organocatalyzed C-glycosylation of indole: implications of acceptor-catalyst-donor interactions [J]. | ORGANIC CHEMISTRY FRONTIERS , 2024 , 12 (2) : 509-515 . |
| MLA | Xie, Lihuang et al. "A stereoselective organocatalyzed C-glycosylation of indole: implications of acceptor-catalyst-donor interactions" . | ORGANIC CHEMISTRY FRONTIERS 12 . 2 (2024) : 509-515 . |
| APA | Xie, Lihuang , Liu, Wenchao , Guo, Zhenbo , Jiao, Qinbo , Shen, Xiaomin , Liu, Tianfei et al. A stereoselective organocatalyzed C-glycosylation of indole: implications of acceptor-catalyst-donor interactions . | ORGANIC CHEMISTRY FRONTIERS , 2024 , 12 (2) , 509-515 . |
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Abstract ：
Previous N-glycosylation approaches have predominately involved acidic conditions, facing challenges of low stereoselectivity and limited scope. Herein, we introduce a radical activation strategy that enables versatile and stereoselective N-glycosylation using readily accessible glycosyl sulfinate donors under basic conditions and exhibits exceptional tolerance towards various N-aglycones containing alkyl, aryl, heteroaryl and nucleobase functionalities. Preliminary mechanistic studies indicate a pivotal role of iodide, which orchestrates the formation of a glycosyl radical from the glycosyl sulfinate and subsequent generation of the key intermediate, a configurationally well-defined glycosyl iodide, which is subsequently attacked by an N-aglycone in a stereospecific SN2 manner to give the desired N-glycosides. An alternative route involving the coupling of a glycosyl radical and a nitrogen-centered radical is also proposed, affording the exclusive 1,2-trans product. This novel approach promises to broaden the synthetic landscape of N-glycosides, offering a powerful tool for the construction of complex glycosidic structures under mild conditions. A versatile and stereoselective N-glycosylation has been developed using glycosyl sulfinates under basic conditions. Mechanistic studies indicate the transformation involves a key glycosyl radical species, which can directly couple with a nitrogen-centered radical. An alternative route involving the coupling of glycosyl and iodine radicals, followed by an SN2 reaction with the resultant glycosyl iodide to give the N-glycoside, is also demonstrated. image
Keyword ：
glycosyl iodides glycosyl iodides glycosyl sulfinates glycosyl sulfinates N-glycosides N-glycosides N-glycosylation N-glycosylation radical reactions radical reactions
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| GB/T 7714 | Ding, Wenyan , Chen, Xinyu , Sun, Zuyao et al. A Radical Activation Strategy for Versatile and Stereoselective N-Glycosylation [J]. | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION , 2024 , 63 (36) . |
| MLA | Ding, Wenyan et al. "A Radical Activation Strategy for Versatile and Stereoselective N-Glycosylation" . | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 63 . 36 (2024) . |
| APA | Ding, Wenyan , Chen, Xinyu , Sun, Zuyao , Luo, Jiaxin , Wang, Shiping , Lu, Qingqing et al. A Radical Activation Strategy for Versatile and Stereoselective N-Glycosylation . | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION , 2024 , 63 (36) . |
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Abstract ：
研究生教育是高等教育的最高层次,是衡量一个国家高等教育竞争力的关键标志,是拔尖创新人才自主培养的主渠道.为了提高人才培养质量,在"以学生为中心,注重科学思维培养,注重科研能力培养以及注重国际视野培养"的教学思想指导下,针对有机结构分析课程教学过程中存在的难点问题,从"教学理念的国际化、教学内容的国际化、教学团队的国际化、教学方法的国际化"等方面进行创新教学实践,取得了一系列成果,有效地提升了学生的科研水平,对于创新型人才的培养起到了积极的推动作用.
Keyword ：
国际化视野 国际化视野 学生为中心 学生为中心 有机结构分析 有机结构分析 研究生教学 研究生教学
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| GB/T 7714 | 袁耀锋 , 叶克印 , 徐春发 et al. 在研究生课程的教学中注重国际视野的培养 [J]. | 大学化学 , 2024 , 39 (6) : 145-150 . |
| MLA | 袁耀锋 et al. "在研究生课程的教学中注重国际视野的培养" . | 大学化学 39 . 6 (2024) : 145-150 . |
| APA | 袁耀锋 , 叶克印 , 徐春发 , 晏宏 , 李远明 . 在研究生课程的教学中注重国际视野的培养 . | 大学化学 , 2024 , 39 (6) , 145-150 . |
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Abstract ：
研究生教育是高等教育的最高层次，是衡量一个国家高等教育竞争力的关键标志，是拔尖创新人才自主培养的主渠道。为了提高人才培养质量，在“以学生为中心，注重科学思维培养，注重科研能力培养以及注重国际视野培养”的教学思想指导下，针对有机结构分析课程教学过程中存在的难点问题，从“教学理念的国际化、教学内容的国际化、教学团队的国际化、教学方法的国际化”等方面进行创新教学实践，取得了一系列成果，有效地提升了学生的科研水平，对于创新型人才的培养起到了积极的推动作用。
Keyword ：
国际化视野 国际化视野 学生为中心 学生为中心 有机结构分析 有机结构分析 研究生教学 研究生教学
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| GB/T 7714 | 袁耀锋 , 叶克印 , 徐春发 et al. 在研究生课程的教学中注重国际视野的培养——以“有机结构分析”课程为例 [J]. | 大学化学 , 2024 , 39 (06) : 145-150 . |
| MLA | 袁耀锋 et al. "在研究生课程的教学中注重国际视野的培养——以“有机结构分析”课程为例" . | 大学化学 39 . 06 (2024) : 145-150 . |
| APA | 袁耀锋 , 叶克印 , 徐春发 , 晏宏 , 李远明 . 在研究生课程的教学中注重国际视野的培养——以“有机结构分析”课程为例 . | 大学化学 , 2024 , 39 (06) , 145-150 . |
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Abstract ：
芳香亲核取代反应被有机化学家广泛地用于有机化合物的合成，是最重要的合成反应之一。教材中对于该反应机理的介绍为分步过程，但是随着研究的深入，通过协同过程的芳香亲核取代反应已经被广泛证实。本文简要回顾了分步进行的芳香亲核取代反应，重点介绍了协同芳香亲核取代反应的几个实例，阐述了反应设计对机理研究的重要性。通过将科研成果融入教学过程，有助于进一步加深对芳香亲核取代反应的理解。
Keyword ：
分步 分步 协同 协同 反应机理 反应机理 芳香亲核取代反应 芳香亲核取代反应
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| GB/T 7714 | 林文涛 , 王文峰 , 袁耀锋 et al. 协同芳香亲核取代反应 [J]. | 大学化学 , 2024 , 39 (06) : 226-230 . |
| MLA | 林文涛 et al. "协同芳香亲核取代反应" . | 大学化学 39 . 06 (2024) : 226-230 . |
| APA | 林文涛 , 王文峰 , 袁耀锋 , 徐春发 . 协同芳香亲核取代反应 . | 大学化学 , 2024 , 39 (06) , 226-230 . |
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A noncovalent organocatalytic concerted addition of phenol to glycal is developed for the stereoselective and regioselective construction of biologically important phenolic 2-deoxyglycosides, featuring wide substrate tolerance. The method relies on an anion-bridged dual hydrogen bond interaction which is experimentally proved by Nuclear Magnetic Resonance (NMR), Ultraviolet and visible (UV-vis), and fluorescence analysis. Experimental evidence including kinetic analysis, Kinetic Isotope Effect (KIE) studies, linear free energy relationship, Hammett plot, and density functional theory (DFT) calculations is provided for a concerted mechanism where a high-energy oxocarbenium ion is not formed. In addition, the potential utility of this method is further demonstrated by the synthesis of biologically active glycosylated flavones. The benchmarking studies demonstrate significant advances in this newly developed method compared to previous approaches. A concerted addition of phenol to glycal promoted by anion-bridged dual hydrogen bond interaction is disclosed, featuring excellent stereoselectivity and broad substrate tolerance. The unprecedented concerted addition pathway is confirmed by kinetic analysis, KIE studies, Hammett plot and DFT calculation. The synthesis of biologically active glycosylated flavones and benchmarking studies demonstrate the significant advance of this method.image
Keyword ：
concerted addition concerted addition glycosylation glycosylation hydrogen bond hydrogen bond organocatalysis organocatalysis phenolic glycoside phenolic glycoside
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| GB/T 7714 | Jiao, Qinbo , Guo, Zhenbo , Zheng, Mingwen et al. Anion-Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal [J]. | ADVANCED SCIENCE , 2024 , 11 (11) . |
| MLA | Jiao, Qinbo et al. "Anion-Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal" . | ADVANCED SCIENCE 11 . 11 (2024) . |
| APA | Jiao, Qinbo , Guo, Zhenbo , Zheng, Mingwen , Lin, Wentao , Liao, Yujie , Yan, Weitao et al. Anion-Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal . | ADVANCED SCIENCE , 2024 , 11 (11) . |
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Correction for 'Cu-catalyzed arylation of S-tosyl peptides with arylboronic acids' by Junjie Ying et al., Org. Chem. Front., 2024, 11, 53-59, https://doi.org/10.1039/D3QO01534C.
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| GB/T 7714 | Ying, Junjie , Huang, Jingrong , Liu, Chenguang et al. Cu-catalyzed arylation of S-tosyl peptides with arylboronic acids (vol 11, pg 53, 2024) [J]. | ORGANIC CHEMISTRY FRONTIERS , 2024 , 11 (8) : 2418-2418 . |
| MLA | Ying, Junjie et al. "Cu-catalyzed arylation of S-tosyl peptides with arylboronic acids (vol 11, pg 53, 2024)" . | ORGANIC CHEMISTRY FRONTIERS 11 . 8 (2024) : 2418-2418 . |
| APA | Ying, Junjie , Huang, Jingrong , Liu, Chenguang , Chen, Fa-Jie , Xu, Chunfa , Chen, Fen-Er . Cu-catalyzed arylation of S-tosyl peptides with arylboronic acids (vol 11, pg 53, 2024) . | ORGANIC CHEMISTRY FRONTIERS , 2024 , 11 (8) , 2418-2418 . |
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