Photoredox-Catalyzed Metal-free Regio- & Stereoselective C(sp 2 )-H Amination of Enamides with N -aminopyridium salts
Year: 2024
Type: preprint
Abstract: 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 in 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 amidyl 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-amino enamides. The operational simplicity, environmentally friendliness and cost efficiency of this methodology has paved a new avenue to enrich the arsenal of synthetically crucial functionalized enamides and their derivatives.
Institution: Nanjing Tech University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W4397039965