A palladium-catalyzed C-H functionalization route to ketones via the oxidative coupling of arenes with carbon monoxide

We describe the development of a new palladium-catalyzed method to generate ketones via the oxidative coupling of two arenes and CO. This transformation is catalyzed by simple palladium salts, and is postulated to proceed via the conversion of arenes into high energy aroyl triflate electrophiles. Ex...

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Published inChemical science (Cambridge) Vol. 11; no. 11; pp. 3104 - 3109
Main Authors Levesque, Taleah M., Kinney, R. Garrison, Arndtsen, Bruce A.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.03.2020
Royal Society of Chemistry
The Royal Society of Chemistry
Subjects
Aromatic compounds
Carbon monoxide
Chemistry
Chemistry, Multidisciplinary
Coupling
Ketones
Palladium
Physical Sciences
Science & Technology
ARYL BROMIDES
CYCLOCARBONYLATION
ACTIVATION
PD
HYDROCARBONS
CARBONYLATION REACTIONS
ACYLATION
BOND FUNCTIONALIZATION
IODINATION
ORTHO-ARYLATION
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Summary:We describe the development of a new palladium-catalyzed method to generate ketones via the oxidative coupling of two arenes and CO. This transformation is catalyzed by simple palladium salts, and is postulated to proceed via the conversion of arenes into high energy aroyl triflate electrophiles. Exploiting the latter can also allow the synthesis of unsymmetrical ketones from two different arenes.
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ISSN:2041-6520
2041-6539
DOI:10.1039/d0sc00085j