ol7b00989_si_001.pdf (18.24 MB)
Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides
journal contribution
posted on 2017-04-26, 19:17 authored by Javad Amani, Rauful Alam, Shorouk Badir, Gary A. MolanderAn
electrophilic, imide-based, visible-light-promoted photoredox/Ni-catalyzed
cross-coupling reaction for the synthesis of aliphatic ketones has
been developed. This protocol proceeds through N–C(O) bond
activation, made possible through the lower activation energy for
metal insertion into this bond due to delocalization of the lone pair
of electrons on the nitrogen by electron-withdrawing groups. The operationally
simple and mild cross-coupling reaction is performed at ambient temperature
and exhibits tolerance for a variety of functional groups.
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Photoredoxaliphatic ketonesambient temperaturemetal insertioncross-coupling reactionVisible-LightphotoredoxvarietyelectrophilicImideSynergisticSynthesiAliphatic Ketonesdelocalizationexhibits toleranceelectron-withdrawing groupsCleavageimide-basedvisible-light-promotedprotocol proceedssynthesisactivation energybond
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