Copper-Catalyzed Stereoselective Direct Olefinic β-C(sp2)−H Imidation of Acyclic Enamides with NFSI

Guisheng Chen; Xiaolan Li; Jie Liu; Haidong Liu; Haiqing Luo

doi:10.1002/cjoc.70118

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (18) : 2347 -2352. DOI: 10.1002/cjoc.70118

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Copper-Catalyzed Stereoselective Direct Olefinic β-C(sp²)−H Imidation of Acyclic Enamides with NFSI

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Abstract

Herein, we reported a copper-catalyzed stereoselective olefinic β-C(sp²)–H imidation of acyclic enamides employing commercially available N-fluorobenzenesulfonimide (NFSI) as an imidating reagent, which allows for the synthesis of various imidation products with mainly E-selective control. This methodology was featured by being ligand-free, having good efficacy, and exhibiting broad substrate scope for acyclic enamides. Mechanistically, the imidyl radical species might be involved in the reaction.

Keywords

Copper catalyst / C–H imidation / Enamides / NFSI / E-selectivity

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Guisheng Chen, Xiaolan Li, Jie Liu, Haidong Liu, Haiqing Luo. Copper-Catalyzed Stereoselective Direct Olefinic β-C(sp²)−H Imidation of Acyclic Enamides with NFSI. Chinese Journal of Chemistry, 2025, 43(18): 2347-2352 DOI:10.1002/cjoc.70118