Photoredox-Catalyzed Metal-Free Regio- & Stereoselective C(sp2)–H Amination of Enamides with N-Aminopyridium Salts
Zheng-Bao Qin , Kun Ni , Li Wang , Xiao-Di Wu , Yu Zhang , Kai Zhao
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (18) : 2235 -2242.
Photoredox-Catalyzed Metal-Free Regio- & Stereoselective C(sp2)–H Amination of Enamides with N-Aminopyridium Salts
A visible-light-induced photoredox-catalyzed regioselective and stereoselective C(sp 2)–H amination of enamides with bench-stable and easily accessible N-aminopyridium salts is developed, affording synthetically and biologically prominent vicinal 1, 2-diamine scaffolds with broad substrate scope and excellent functional group compatibility. The transformation proceeded through a radical pathway involving the Giese addition of the relatively electrophilic N-centered sulfonamidyl radical species to nucleophilic β-olefinic position of enamides followed by the ensuing single electron oxidation and β-H elimination, delivering geometrically-defined Z-configured β-sulfonamidylated enamides. The operational simplicity, environmental friendliness and cost efficiency of this methodology allowed it to pave a new avenue to enrich the arsenal of synthetically crucial functionalized enamides and their related derivatives.
Enamides / Amination / Photoredox catalysis / Regioselective / Stereoselective / Metal-free
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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