Carbonylation of Alkyl Radicals Derived from Organosilicates through Visible‐Light Photoredox Catalysis

Primary, secondary, and tertiary alkyl radicals formed by the photocatalyzed oxidation of organosilicates underwent efficient carbonylation with carbon monoxide (CO) to give a variety of unsymmetrical ketones. This study introduces the possibility of radical carbonylation under a photooxidative regi...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-02, Vol.58 (6), p.1789-1793
Main Authors: Cartier, Alex, Levernier, Etienne, Corcé, Vincent, Fukuyama, Takahide, Dhimane, Anne‐Lise, Ollivier, Cyril, Ryu, Ilhyong, Fensterbank, Louis
Format: Article
Language:English
Subjects:
Carbon monoxide
carbonylation
Carbonyls
Catalysis
Ketones
Oxidation
photocatalysis
Photoredox catalysis
Radicals
silicates
three-component reactions
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Summary:Primary, secondary, and tertiary alkyl radicals formed by the photocatalyzed oxidation of organosilicates underwent efficient carbonylation with carbon monoxide (CO) to give a variety of unsymmetrical ketones. This study introduces the possibility of radical carbonylation under a photooxidative regime. Advocating a regime change: Primary, secondary, and tertiary alkyl radicals, formed by the photocatalyzed oxidation of organosilicates, underwent three‐component reactions with carbon monoxide (CO) and radical acceptors to provide unsymmetrical ketones (see scheme). The concept of radical carbonylation under a photooxidative regime and metal‐free conditions has significant potential more generally for photocatalytic carbonylation reactions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201811858