Journal
GREEN CHEMISTRY
Volume 25, Issue 10, Pages 4129-4136Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d3gc00054k
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This paper reports the photoinduced generation of highly reactive ketyl radicals and their application in C-C coupling, without the need for any external photocatalyst.
Single-electron reduction of a carbonyl by photoredox catalysis enables the generation of ketyl radicals, providing a benign procedure for constructing C-C bonds. However, external photocatalysts are required. In this paper, photoinduced generation of ketyl radicals and application in C-C coupling are reported, which require no use of any external photocatalyst. Irradiation of carbonyl with purple light in the presence of a tertiary amine generates highly reactive ketyl radicals, enabling a series of important reactions in synthetic chemistry, such as the reductive coupling of aldehydes, ketones, and imines, the allylation of aldehydes, the Barbier reaction, reductive arylation, and aldehyde-aniline coupling. We also present evidence to support the ketyl radicals being formed via photoinduced intermolecular electron transfer from the tertiary amine to aryl aldehydes.
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