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学者姓名：刘晨光
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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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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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