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学者姓名：徐春发
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Abstract ：
Glycosyl sulfonamides have been identified as novel inhibitors of carbonic anhydrase, showing great potential for cancer treatment. However, previous approaches to synthesizing glycosyl sulfonamides require multi steps, resulting in low efficiency and being time-consuming. Herein, we disclose a reductive coupling strategy that enables the modular synthesis of glycosyl sulfonamide using readily accessible glycosyl sulfinates and feedstock chemical nitroarenes. This method allows for the construction of rarely reported N-aryl glycosyl sulfonamides and exhibits tolerance to a variety of functional groups.
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| GB/T 7714 | Zhen, Wenxu , Ma, Jialu , Ni, Zhaohui et al. Modular synthesis of glycosyl sulfonamide via reductive coupling of glycosyl sulfinate and nitroarene [J]. | NEW JOURNAL OF CHEMISTRY , 2025 , 49 (9) : 3416-3421 . |
| MLA | Zhen, Wenxu et al. "Modular synthesis of glycosyl sulfonamide via reductive coupling of glycosyl sulfinate and nitroarene" . | NEW JOURNAL OF CHEMISTRY 49 . 9 (2025) : 3416-3421 . |
| APA | Zhen, Wenxu , Ma, Jialu , Ni, Zhaohui , Luo, Jiaxin , Shen, Xiaomin , Xie, Yusheng et al. Modular synthesis of glycosyl sulfonamide via reductive coupling of glycosyl sulfinate and nitroarene . | NEW JOURNAL OF CHEMISTRY , 2025 , 49 (9) , 3416-3421 . |
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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 et al. "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 ：
Glycosyl aryl sulfones have gained significant attention due to their diverse range of biological activities. However, a straightforward synthesis under mild conditions remains a challenging endeavor. This work presents the first transition-metal-free glycosyl sulfonation, employing a readily prepared sodium glycosyl sulfinate in conjunction with diaryliodonium salts. The method is compatible with various sugar substrates including unprotected sugar derivatives. Notably, the transfer of an aryl moiety in unsymmetric diaryl iodonium salts is chemoselectively achieved by utilizing an anisyl or TMP fragment as a dummy ligand. Preliminary mechanistic studies suggest that the reaction may proceed through an intramolecular SNAr process with a four-membered ring transition state. Transition-metal-free glycosyl sulfonation employing a readily prepared sodium glycosyl sulfinate in conjunction with diaryliodonium salts was reported, featuring wide tolerance with unprotected sugar substrates.
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| GB/T 7714 | Luo, Jiaxin , Chen, Xinyu , Ding, Wenyan et al. Transition-metal-free glycosyl sulfonation of diaryliodonium salts with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones [J]. | NEW JOURNAL OF CHEMISTRY , 2024 , 48 (10) : 4218-4223 . |
| MLA | Luo, Jiaxin et al. "Transition-metal-free glycosyl sulfonation of diaryliodonium salts with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones" . | NEW JOURNAL OF CHEMISTRY 48 . 10 (2024) : 4218-4223 . |
| APA | Luo, Jiaxin , Chen, Xinyu , Ding, Wenyan , Ma, Jialu , Ni, Zhaohui , Xie, Lihuang et al. Transition-metal-free glycosyl sulfonation of diaryliodonium salts with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones . | NEW JOURNAL OF CHEMISTRY , 2024 , 48 (10) , 4218-4223 . |
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Abstract ：
Correction for 'Transition-metal-free glycosyl sulfonation of diaryliodonium salts with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones' by Jiaxin Luo et al., New J. Chem., 2024, 48, 4218-4223, https://doi.org/10.1039/D3NJ05942A.
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| GB/T 7714 | Luo, Jiaxin , Chen, Xinyu , Ding, Wenyan et al. Transition-metal-free glycosyl sulfonation of diaryliodonium salts with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones (vol 48, pg 4218, 2024) [J]. | NEW JOURNAL OF CHEMISTRY , 2024 , 48 (15) : 7021-7021 . |
| MLA | Luo, Jiaxin et al. "Transition-metal-free glycosyl sulfonation of diaryliodonium salts with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones (vol 48, pg 4218, 2024)" . | NEW JOURNAL OF CHEMISTRY 48 . 15 (2024) : 7021-7021 . |
| APA | Luo, Jiaxin , Chen, Xinyu , Ding, Wenyan , Ma, Jialu , Ni, Zhaohui , Xie, Lihuang et al. Transition-metal-free glycosyl sulfonation of diaryliodonium salts with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones (vol 48, pg 4218, 2024) . | NEW JOURNAL OF CHEMISTRY , 2024 , 48 (15) , 7021-7021 . |
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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 ：
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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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 ：
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 ：
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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