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α‐Aminoxy‐Acid‐Auxiliary‐Enabled Intermolecular Radical γ‐C(sp 3 )−H Functionalization of Ketones
Author(s) -
Jiang Heng,
Studer Armido
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201712066
Subject(s) - chemistry , radical , surface modification , imine , regioselectivity , photoredox catalysis , hydrogen atom abstraction , ketone , catalysis , photochemistry , intermolecular force , combinatorial chemistry , organic chemistry , molecule , photocatalysis
A method for site‐specific intermolecular γ‐C(sp 3 )−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.