Photoinduced Copper-Catalyzed 1,2-Difunctionalization of 1,3-Dienes with Aryl Diselenides

Photoinduced Copper-Catalyzed 1,2-Difunctionalization of 1,3-Dienes with Aryl Diselenides

Described herein is a photoinduced copper-catalyzed 1,2-difunctionalization of 1,3-dienes. The selenium atom radical was generated by the visible light irradiation of diselenides, triggering radical addition with 1,3-dienes to form allyl radical intermediate. Subsequent rapid Z/E isomerization allow...

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Veröffentlicht in:Journal of organic chemistry 2023-11, Vol.88 (22), p.15969-15974
Hauptverfasser: Guo, Shengkun, Shen, Xiaoyu, Chen, Xiaoyun, Yu, Huaguang, Han, Ying, Yan, Chaoguo, Shi, Yaocheng, Hou, Hong, Zhu, Shaoqun
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Sprache:eng
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Zusammenfassung:Described herein is a photoinduced copper-catalyzed 1,2-difunctionalization of 1,3-dienes. The selenium atom radical was generated by the visible light irradiation of diselenides, triggering radical addition with 1,3-dienes to form allyl radical intermediate. Subsequent rapid Z/E isomerization allowed for thermodynamically favorable intermediate formation and enabled copper catalyzed stereoselective functionalization with various nucleophiles.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01181