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学者姓名：刘晨光
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Abstract ：
Aftobetin is a non-invasive diagnosis of Alzheimer ' s disease, that can bind with aggregated beta-amyloid peptide in eye ' s lenses, used for early diagnosis of Alzheimer ' s disease in a rapid and painless mode. The reported synthesis of this probe fell short in the aspects of greenness and economy due to the involvement of toxic Chromium(IV) oxidant, noble palladium catalyst, elevated reaction temperature, the long reaction time as well as the cumbersome workup. Herein, a holistic optimization of the synthetic process was achieved via the employment of flow technology and heterogenous photocatalysis. Firstly, the integration of heterogenous carbon nitrides photocatalysis and circulation flow technology furnished the air oxidation of alcohol and nickel catalyzed C-N coupling at 20 g scale, thus avoiding the use of toxic Chromium and precious palladium species respectively. Flow-intensified esterification between acyl chloride and alcohol, just taking 30 seconds replaced the Steglich esterification of 6 hours, also avoiding the generation of difficult-to-remove dicyclohexylurea. Finally, C-N coupling, esterification and Knoevenagel condensation were telescoped together, thus simplifying the reaction workup. This fully-flow protocol led to the on-demand synthesis of eight probes.
Keyword ：
AD probes AD probes Aftobetin Aftobetin Flow synthesis technology Flow synthesis technology Heterogenous photocatalysis Heterogenous photocatalysis
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| GB/T 7714 | Li, Yongjiu , Liu, Xin , Liu, Qiong et al. Green Synthesis of Alzheimer′s Disease Probes Aftobetin and Analogues Enabled by Flow Technology and Heterogeneous Photocatalysis [J]. | CHEMSUSCHEM , 2025 , 18 (1) . |
| MLA | Li, Yongjiu et al. "Green Synthesis of Alzheimer′s Disease Probes Aftobetin and Analogues Enabled by Flow Technology and Heterogeneous Photocatalysis" . | CHEMSUSCHEM 18 . 1 (2025) . |
| APA | Li, Yongjiu , Liu, Xin , Liu, Qiong , Wang, Yuchen , Liu, Chenguang , Chen, Fener . Green Synthesis of Alzheimer′s Disease Probes Aftobetin and Analogues Enabled by Flow Technology and Heterogeneous Photocatalysis . | CHEMSUSCHEM , 2025 , 18 (1) . |
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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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Abstract ：
Although continuous flow synthesis using microtubing reactors has provided a wealth of opportunities for homogeneous photochemical synthesis and has proven particularly beneficial in scaling up processes, employing continuous flow technology to scale up heterogeneous photoreactions is challenging due to the issues including handling of solids, poor light penetration, and commonly lengthy reaction time. Here we present a solution to these issues by changing the continuous flow mode to a high-speed circulation flow mode. The high flow rate set in a circulation flow reactor overcomes solid sedimentation to prevent clogging and improve the mixing efficiency. We successfully conducted 100 g-scale C-N and C-S cross-couplings using a heterogeneous photocatalyst and a nickel catalyst in the flow reactor that significantly outperformed conventional batch reactors. The photocatalyst was recycled and reused 10 times to achieve a kilogram-scale synthesis without obvious deactivation. Semicontinuous production was achieved via automated feeding and collection, and a photopromoted gas/liquid/solid three-phase trifluoromethylation reaction was employed. A kilogram-scale amount of starting material was successfully transformed, resulting in a 43.2% yield of trifluridine. Our study suggests that a circulation flow reactor with high flow speed will become a crucial tool in the synthetic chemist's toolbox because of its simple infrastructure, ease of operation and automation, significant efficiency improvement compared to conventional batch reactors, scalability, improved safety, and tolerance of solids.
Keyword ：
autonomous feeding and collecting autonomous feeding and collecting gas/liquid/solidthree-phase reaction gas/liquid/solidthree-phase reaction high-speed circulationflow high-speed circulationflow kilogram-scale synthesis kilogram-scale synthesis tolerance of solids tolerance of solids
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| GB/T 7714 | Liu, Chenguang , Song, Lei , Liu, Qiong et al. High-Speed Circulation Flow Platform Facilitating Practical Large-Scale Heterogeneous Photocatalysis [J]. | ORGANIC PROCESS RESEARCH & DEVELOPMENT , 2024 , 28 (5) : 1964-1970 . |
| MLA | Liu, Chenguang et al. "High-Speed Circulation Flow Platform Facilitating Practical Large-Scale Heterogeneous Photocatalysis" . | ORGANIC PROCESS RESEARCH & DEVELOPMENT 28 . 5 (2024) : 1964-1970 . |
| APA | Liu, Chenguang , Song, Lei , Liu, Qiong , Chen, Weihao , Xu, Jinhui , Wang, Mu et al. High-Speed Circulation Flow Platform Facilitating Practical Large-Scale Heterogeneous Photocatalysis . | ORGANIC PROCESS RESEARCH & DEVELOPMENT , 2024 , 28 (5) , 1964-1970 . |
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Transition metal-mediated S-arylation has emerged as a powerful tool for the synthesis of S-arylcysteine and S-arylpeptide, which are useful building blocks in pharmacophores and biomolecules. In contrast, the catalytic protocols for arylation remain unexplored, particularly methods employing abundant metal catalysts (e.g. Cu and Ni). Herein, we reported the copper-catalyzed arylation chemistry of S-tosyl peptides with readily available arylboronic acids. This method features excellent yields and a wide variety of aryl groups, enabling the efficient synthesis of S-arylated cysteines and peptides under mild reaction conditions (room temperature, weak base). The reaction can be carried out in both batch and flow, demonstrating its utility in organic synthesis.
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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 [J]. | ORGANIC CHEMISTRY FRONTIERS , 2023 , 11 (1) : 53-59 . |
| MLA | Ying, Junjie et al. "Cu-catalyzed arylation of S-tosyl peptides with arylboronic acids" . | ORGANIC CHEMISTRY FRONTIERS 11 . 1 (2023) : 53-59 . |
| 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 . | ORGANIC CHEMISTRY FRONTIERS , 2023 , 11 (1) , 53-59 . |
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