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Synthesis of Sterically Hindered α-Hydroxycarbonyls through Radical-Radical Coupling

Kenji Ota, Kazunori Nagao* and Hirohisa Ohmiya*

*Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan, Email: nkazunorip.kanazawa-u.ac.jp, ohmiyap.kanazawa-u.ac.jp

K. Ota, K. Nagao, H. Ohmiya, Org. Lett., 2021, 23, 4420-4425.

DOI: 10.1021/acs.orglett.1c01358



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Abstract

An organic photoredox catalysis reaction converts aliphatic carboxylic acids to transient alkyl radicals and α-ketocarbonyls to persistent ketyl radicals, which couple selectively under mild reaction conditions based on the persistent radical effect. Primary, secondary, and tertiary aliphatic carboxylic acids can used to introduce various alkyl substituents.


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proposed mechanism


4CzIPN



Key Words

α-hydroxy esters, photochemistry


ID: J54-Y2021