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Visible Light‐Induced Copper‐Catalyzed Alkylation/exo‐Cyclization of 1,7‐Dienes with Sulfonium Salts to Access Sulfur‐Containing Polycyclic Compounds
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2024-07-09 , DOI: 10.1002/adsc.202400445
Xin-Qian Liu 1 , Jian-Hong Fan 2 , Kewen Tang 1 , Long-Jin Zhong 1 , Yu Liu 1
Affiliation  

A direct visible‐light‐promoted radical‐triggered tandem cyclization of 1,7‐diene systems with cyclic sulfonium salts by using copper(I)‐based complexes as photoredox catalyst is developed. With this approach, a variety of sulfur‐containing polycyclic derivatives are prepared through alkylation/6‐exo‐trig cyclization/5‐exo‐trig cyclization of 1,7‐diene systems under mild conditions. In addition, the photoinduced copper‐catalyzed ring‐opening of cyclic sulfonium salts provides the alkyl radical intermediates, which prefers addition to the Ph‐linked C‐C double bond rather than the electron‐deficient vinyl in 1,7‐dienes. Moreover, oxidation of the desire sulfur‐containing polycyclic products provides a strategy for the preparation of remote nitrogen‐fused polycyclic substituted sulfoxide or sulfone‐containing derivatives.

中文翻译:


可见光诱导铜催化 1,7-二烯与锍盐的烷基化/外环化反应生成含硫多环化合物



通过使用铜(I)基配合物作为光氧化还原催化剂,开发了一种直接可见光促进的自由基触发的1,7-二烯体系与环状锍盐的串联环化反应。通过该方法,在温和条件下通过1,7-二烯体系的烷基化/6-外三环化/5-外三环化制备了多种含硫多环衍生物。此外,光诱导的铜催化环状锍盐开环提供了烷基自由基中间体,该中间体更倾向于加成到Ph连接的C-C双键上,而不是1,7-二烯中的缺电子乙烯基上。此外,所需含硫多环产物的氧化为制备远程氮稠合多环取代的亚砜或含砜衍生物提供了策略。
更新日期:2024-07-09
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