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  • Title: A Photochemical Organocatalytic Strategy for the α-Alkylation of Ketones by using Radicals.
    Author: Spinnato D, Schweitzer-Chaput B, Goti G, Ošeka M, Melchiorre P.
    Journal: Angew Chem Int Ed Engl; 2020 Jun 08; 59(24):9485-9490. PubMed ID: 32053279.
    Abstract:
    Reported herein is a visible-light-mediated radical approach to the α-alkylation of ketones. This method exploits the ability of a nucleophilic organocatalyst to generate radicals upon SN 2-based activation of alkyl halides and blue light irradiation. The resulting open-shell intermediates are then intercepted by weakly nucleophilic silyl enol ethers, which would be unable to directly attack the alkyl halides through a traditional two-electron path. The mild reaction conditions allowed functionalization of the α position of ketones with functional groups that are not compatible with classical anionic strategies. In addition, the redox-neutral nature of this process makes it compatible with a cinchona-based primary amine catalyst, which was used to develop a rare example of enantioselective organocatalytic radical α-alkylation of ketones.
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