Photoinduced Copper-Catalyzed Aminoalkylation of Amino-Pendant Olefins

• Published in: Organic letters Vol. 25; no. 31; pp. 5862 - 5868
• Main Authors: Zhang, Can-Can, Wu, Hong-Li, Yu, Xuan-Chi, Wang, Ling-Tao, Zhou, Yu, Sun, Yong-Bin, Wei, Wen-Ting
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 11.08.2023; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; PHOTOREDOX; ALKYLATION; EFFICIENT SYNTHESIS; CASCADE SYNTHESIS; ENABLES; CYCLIZATION; UNACTIVATED ALKENES
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/acs.orglett.3c02119

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.