Journal
ORGANIC LETTERS
Volume 21, Issue 24, Pages 9940-9944Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03871
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Funding
- NIGMS [R35 GM126986]
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A general protocol for the hydroacylation of styrenes from aliphatic carboxylic acids is reported: These reactions proceed via beta-scission of a phosphoranyl radical that is accessed by photoredox catalysis, followed by addition of the resulting acyl radical to the styrenyl olefin. We show that phosphine tunability is critical for efficient intermolecular coupling due to competitive quenching of the photocatalyst by the olefin. Primary, secondary, and structurally rigid tertiary carboxylic acids all generate valuable unsymmetrical dialkyl ketones.
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