Zhang Wenjuan, Song Yaqi, Sun Tian-Yu, Wang Dawei, Xia Xiao-Feng
Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu 214122, China.
Institute of Chemical Biology, Shenzhen Bay Laboratory, Shenzhen 518132, China.
J Org Chem. 2024 Apr 5;89(7):5060-5068. doi: 10.1021/acs.joc.4c00282. Epub 2024 Mar 25.
Radical cyclization has been demonstrated to be an efficient method to access functionalized heterocycles from easily accessible raw materials. Described herein is the development of a photocatalytic proton-coupled electron transfer (PCET) strategy for the synthesis of isoquinoline-1,3-diones using readily prepared naphthalimide (NI)-based organic photocatalysts. The process features free metal-complex photocatalysts, acids, and mild reaction conditions. This mild radical cyclization protocol has a broad substrate scope and can be effectively applied to a variety of medicinally relevant substrates. Furthermore, control experiments were conducted to elucidate the mechanism of this visible light-induced methodology.
自由基环化已被证明是一种从易于获取的原料制备功能化杂环的有效方法。本文描述了一种光催化质子耦合电子转移（PCET）策略的开发，该策略使用易于制备的基于萘二甲酰亚胺（NI）的有机光催化剂来合成异喹啉-1,3-二酮。该过程的特点是无需金属配合物光催化剂、酸，且反应条件温和。这种温和的自由基环化方案具有广泛的底物范围，可有效地应用于各种与药物相关的底物。此外，还进行了对照实验以阐明这种可见光诱导方法的机理。
