American Chemical Society
ol3c02119_si_001.pdf (3.87 MB)

Photoinduced Copper-Catalyzed Aminoalkylation of Amino-Pendant Olefins

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journal contribution
posted on 2023-08-03, 11:05 authored by Can-Can Zhang, Hong-Li Wu, Xuan-Chi Yu, Ling-Tao Wang, Yu Zhou, Yong-Bin Sun, Wen-Ting Wei
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.