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Cyclic Amine Synthesis via Catalytic Radical-Polar Crossover Cycloadditions
2024-04-24
发表期刊ANGEWANDTE CHEMIE - INTERNATIONAL EDITION (IF:16.1[JCR-2023],16.2[5-Year])
ISSN1433-7851
EISSN1521-3773
卷号63期号:18
发表状态已发表
DOI10.1002/anie.202401671
摘要

The rapid assembly of valuable cyclic amine architectures in a single step from simple precursors has been recognized as an ideal platform in term of efficiency and sustainability. Although a vast number of studies regarding cyclic amine synthesis has been reported, new synthetic disconnection approaches are still high in demand. Herein, we report a catalytic radical-polar crossover cycloaddition to cyclic amine synthesis triggered from primary sulfonamide under photoredox condition. This newly developed disconnection, comparable to established synthetic approaches, will allow to construct β, β-disubstituted cyclic amine and β-monosubstituted cyclic amine derivatives efficiently. This study highlights the unique utility of primary sulfonamide as a bifunctional reagent, which acts as a radical precursor and a nucleophile. The open-shell methodology demonstrates broad tolerance to various functional groups, drug derivatives and natural products in an economically and sustainable fashion. © 2024 Wiley-VCH GmbH.

关键词Drug products Sulfur compounds Amine synthesis Bifunctional reagents Condition Cyclic amines Cycloadditions Radical Radical-polar Simple++ Single-step Sulphonamides
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收录类别EI ; SCI
语种英语
资助项目null[22201179]
WOS研究方向Chemistry
WOS类目Chemistry, Multidisciplinary
WOS记录号WOS:001185234800001
出版者John Wiley and Sons Inc
EI入藏号20241215754274
EI主题词Cycloaddition
EI分类号802.2 Chemical Reactions
原始文献类型Article in Press
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文献类型期刊论文
条目标识符https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/359852
专题物质科学与技术学院
物质科学与技术学院_硕士生
物质科学与技术学院_博士生
物质科学与技术学院_PI研究组_黄焕明组
通讯作者Huang, Huan-Ming
作者单位
School of Physical Science and Technology, ShanghaiTech University, 393 Middle Huaxia Road, Pudong, Shanghai; 201210, China
第一作者单位物质科学与技术学院
通讯作者单位物质科学与技术学院
第一作者的第一单位物质科学与技术学院
推荐引用方式
GB/T 7714
Zhang, Ying,Chen, Shu-Sheng,Li, Kai-Dian,et al. Cyclic Amine Synthesis via Catalytic Radical-Polar Crossover Cycloadditions[J]. ANGEWANDTE CHEMIE - INTERNATIONAL EDITION,2024,63(18).
APA Zhang, Ying,Chen, Shu-Sheng,Li, Kai-Dian,&Huang, Huan-Ming.(2024).Cyclic Amine Synthesis via Catalytic Radical-Polar Crossover Cycloadditions.ANGEWANDTE CHEMIE - INTERNATIONAL EDITION,63(18).
MLA Zhang, Ying,et al."Cyclic Amine Synthesis via Catalytic Radical-Polar Crossover Cycloadditions".ANGEWANDTE CHEMIE - INTERNATIONAL EDITION 63.18(2024).
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