Photoredox/Nickel Dual-Catalyzed Stereoselective Synthesis of Distal Cyano-Substituted Enamides

Herein, the efficient photoredox/nickel dual-catalyzed cyanoalkylation reaction of enamides is illustrated. A wide scope of enamides and cycloketone oxime esters was well-tolerated, affording the synthetically versatile and geometrically defined β-cyanoalkylated enamide scaffolds. The synthetic prac...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-01, Vol.88 (1), p.513-524
Main Authors: Lu, Xiao-Yu, Wang, Jun-Chao, Sun, Xiao-Mei, Gao, Meng-Ting, Ying, Weng-Jing, Ge, Meng-Yuan, Wei, Zheng-Huan, Liu, Zi, Chen, Xing-Ke
Format: Article
Language:English
Subjects:
Amides
Catalysis
Molecular Structure
Nickel
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Summary:Herein, the efficient photoredox/nickel dual-catalyzed cyanoalkylation reaction of enamides is illustrated. A wide scope of enamides and cycloketone oxime esters was well-tolerated, affording the synthetically versatile and geometrically defined β-cyanoalkylated enamide scaffolds. The synthetic practicality of this protocol was revealed by gram-scale reactions, further transformations of enamides, and late-stage modifications of biologically active molecules.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02497