Zhang Can-Can, Wu Hong-Li, Yu Xuan-Chi, Wang Ling-Tao, Zhou Yu, Sun Yong-Bin, Wei Wen-Ting
School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. China.
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, Hangzhou, Zhejiang 310024, P. R. China.
Org Lett. 2023 Aug 11;25(31):5862-5868. doi: 10.1021/acs.orglett.3c02119. Epub 2023 Aug 3.
The combination of photo and copper catalysts has emerged as a novel paradigm in organic catalysis, which provides access to the acceleration of chemical synthesis. Herein, we describe an aminoalkylation of amino-dependent olefins with maleimides through a cooperative photo/copper catalytic system. In this report, the strategy allows the generation of a broad complex of functionalized nitrogenous molecules including oxazolidinones, 2-pyrrolidones, imidazolidinones, thiazolidinones, pyridines, and piperidines in the absence of an external photosensitizer and base. The approach is achieved through a photoinduced Cu(I)/Cu(II)/Cu(III) complex species of nitrogen nucleophiles, intermolecular radical addition, and hydrogen atom transfer (HAT) processes. The plausible mechanism is investigated by a series of control experiments and theoretical tests, including radical scavenging experiments, deuterium labeling experiments, ultraviolet-visible absorption, and cyclic voltammetry (CV) tests.
光催化剂与铜催化剂的结合已成为有机催化领域的一种新范式，为加速化学合成提供了途径。在此，我们描述了通过光/铜协同催化体系，使依赖氨基的烯烃与马来酰亚胺进行氨基烷基化反应。在本报告中，该策略能够在无需外部光敏剂和碱的情况下，生成包括恶唑烷酮、2-吡咯烷酮、咪唑烷酮、噻唑烷酮、吡啶和哌啶在内的多种功能化含氮分子的广泛复合物。该方法是通过氮亲核试剂的光诱导Cu(I)/Cu(II)/Cu(III)络合物物种、分子间自由基加成和氢原子转移（HAT）过程实现的。通过一系列对照实验和理论测试，包括自由基清除实验、氘标记实验、紫外可见吸收和循环伏安法（CV）测试，对可能的反应机理进行了研究。
