Published December 20, 2019
| Supplemental Material
Journal Article
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Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes To Generate Dialkyl Ketones
Abstract
A general protocol for the hydroacylation of styrenes from aliphatic carboxylic acids is reported. These reactions proceed via β-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.
Additional Information
© 2019 American Chemical Society. Received: October 30, 2019; Published: November 21, 2019. We thank the MacMillan lab (Princeton University) for access to their photoreactors and Lotus Separations for assistance with a purification. Financial support for this project was provided by NIGMS R35 GM126986. The authors declare no competing financial interest.Attached Files
Supplemental Material - ol9b03871_si_001.pdf
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Additional details
- Eprint ID
- 100755
- DOI
- 10.1021/acs.orglett.9b03871
- Resolver ID
- CaltechAUTHORS:20200116-094012400
- R35 GM126986
- NIH
- Created
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2020-01-16Created from EPrint's datestamp field
- Updated
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2021-11-16Created from EPrint's last_modified field