α-Aminoxy-Acid-Auxiliary-Enabled Intermolecular Radical γ-C(sp3 )-H Functionalization of Ketones.
A method for site-specific intermolecular γ-C(sp3 )-H functionalization of ketones has been developed using an α-aminoxy acid auxiliary applying photoredox catalysis. Regioselective activation of an inert C-H bond is achieved by 1,5-hydrogen atom abstraction by an oxidatively generated iminyl radical. Tertiary and secondary C-radicals thus formed at the γ-position of the imine functionality undergo radical conjugate addition to various Michael acceptors to provide, after reduction and imine hydrolysis, the corresponding γ-functionalized ketones.
['Jiang|Heng|H|', 'Studer|Armido|A|0000-0002-1706-513X']
ketone iminyl radical C−H bond functionalization photoredox chemistry redox-neutral