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可见光介导的苯胺与磺酰氟的磺酰化反应。

Visible-light-mediated sulfonylation of anilines with sulfonyl fluorides.

作者信息

Li Xin-Qing, Liao Qian-Qian, Lai Jun, Liao Yuan-Yue

机构信息

Department of Pharmacy, Ganzhou People's Hospital, The Affiliated Ganzhou Hospital of Nanchang University, Ganzhou, China.

Department of Pharmacy, People's Hospital of Guilin, Guilin, China.

出版信息

Front Chem. 2023 Aug 25;11:1267223. doi: 10.3389/fchem.2023.1267223. eCollection 2023.

DOI:10.3389/fchem.2023.1267223
PMID:37693172
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10485258/
Abstract

Sulfonylaniline motif plays an important role in pharmaceutical sciences. Developed methods towards this structure are typically lack of good modifiability and stability. In this study, visible-light-mediated sulfonylation of aniline using sulfonyl fluoride as a modifiable and stable sulfonylation reagent is described. A variety of substituted sulfonylanilines were synthesized under mild reaction conditions with moderate to good efficiency. The example of late-stage sulfonylation highlighted the advantage of using sulfonyl fluoride as a sulfonylation reagent. In addition, the crucial influence of counterions on the photocatalyst observed in this system would inspire further research on the photochemistry of sulfonyl fluoride.

摘要

磺酰苯胺基序在药物科学中起着重要作用。针对这种结构已开发的方法通常缺乏良好的可修饰性和稳定性。在本研究中,描述了使用磺酰氟作为可修饰且稳定的磺酰化试剂,通过可见光介导的苯胺磺酰化反应。在温和的反应条件下,以中等至良好的效率合成了多种取代的磺酰苯胺。后期磺酰化的实例突出了使用磺酰氟作为磺酰化试剂的优势。此外,在该体系中观察到的抗衡离子对光催化剂的关键影响将激发对磺酰氟光化学的进一步研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/029c/10485258/5223feb49327/fchem-11-1267223-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/029c/10485258/03450b72461e/fchem-11-1267223-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/029c/10485258/a56dca03befc/fchem-11-1267223-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/029c/10485258/70d0c3eeea55/fchem-11-1267223-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/029c/10485258/ae8c81cd1913/fchem-11-1267223-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/029c/10485258/5223feb49327/fchem-11-1267223-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/029c/10485258/03450b72461e/fchem-11-1267223-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/029c/10485258/a56dca03befc/fchem-11-1267223-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/029c/10485258/70d0c3eeea55/fchem-11-1267223-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/029c/10485258/ae8c81cd1913/fchem-11-1267223-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/029c/10485258/5223feb49327/fchem-11-1267223-g005.jpg

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本文引用的文献

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Chem Commun (Camb). 2023 Mar 28;59(26):3821-3826. doi: 10.1039/d2cc06339e.
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Safety and efficacy of vebicorvir administered with entecavir in treatment-naïve patients with chronic hepatitis B virus infection.在初治慢性乙型肝炎病毒感染患者中,韦比科韦与恩替卡韦联合使用的安全性和有效性。
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Hydrosulfonylation of Alkenes with Sulfonyl Imines via Ir/Cu Dual Photoredox Catalysis.
通过铱/铜双光氧化还原催化实现烯烃与磺酰亚胺的氢磺酰化反应。
Org Lett. 2022 Jun 10;24(22):3944-3949. doi: 10.1021/acs.orglett.2c01260. Epub 2022 May 26.
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Visible-Light-Mediated Late-Stage Sulfonylation of Anilines with Sulfonamides.可见光促进的苯胺与磺酰胺的晚期磺化反应。
Org Lett. 2022 Jan 28;24(3):853-858. doi: 10.1021/acs.orglett.1c04144. Epub 2022 Jan 20.
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Catalyst-free arylation of sulfonamides visible light-mediated deamination.无催化剂的磺酰胺芳基化:可见光介导的脱氨基反应
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