Journal
ACS CATALYSIS
Volume 12, Issue 2, Pages 1375-1381Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c05124
Keywords
photoredox catalyst; visible light; enone; bromine radical; allylic C-H bond oxidation
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Funding
- National Natural Science Foundation of China [21502086, 21904055]
- Natural Science Foundation of Fujian Province [2019J01744]
- Key Project of Foundation of Fujian Province [2020J02044]
- Natural Science Foundation of Zhangzhou City [ZZ2021J13]
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A practical and efficient method for the direct oxidation of allylic C-H bonds has been established using visible-light-enabled photoredox agents. This metal-free protocol utilizes oxygen as the sole oxidant to produce functionalized enones at room temperature. When combined with acid-promoted dehydration, it enables the production of meta-functionalized phenols from simple cyclohexenols.
A practical and efficient method has been established for the direct oxidation of allylic C-H bonds catalyzed by visible-light-enabled photoredox agents. This protocol uses oxygen as the sole oxidant under metal-free conditions at room temperature and produces functionalized enones. When combined with acid-promoted dehydration, this benign and mild method enables the production of meta-functionalized phenols from simple cyclohexenols. A key to this reaction is the choice of tetrabutylammonium bromide as a hydrogen atom transfer cocatalyst.
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