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. 2018 Feb 5;57(6):1692-1696.
doi: 10.1002/anie.201712066. Epub 2018 Jan 15.

α-Aminoxy-Acid-Auxiliary-Enabled Intermolecular Radical γ-C(sp3 )-H Functionalization of Ketones

Heng Jiang  1 , Armido Studer  1
Affiliations

α-Aminoxy-Acid-Auxiliary-Enabled Intermolecular Radical γ-C(sp3 )-H Functionalization of Ketones

Heng Jiang et al. Angew Chem Int Ed Engl. .

Abstract

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.

Keywords: C−H bond functionalization; iminyl radical; ketone; photoredox chemistry; redox-neutral.

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