Redox-neutral tri-/difluoromethylation of para-quinone methides with sodium sulfinates

The radical tri-/difluoromethylation of para-quinone methides with readily available sodium tri-/difluoromethanesulfinate via organic photoredox catalysis is described. This reaction is external oxidant free and exhibits wide functional group compatibility, providing the desired products in useful y...

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Bibliographic Details
Published inORGANIC CHEMISTRY FRONTIERS Vol. 5; no. 13; pp. 2061 - 2064
Main Authors Wu, Qing-Yan, Ao, Gui-Zhen, Liu, Feng
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.07.2018
Royal Society of Chemistry
Subjects
Catalysis
Chemistry
Chemistry, Organic
Fluorine
Functional groups
Organic chemistry
Photoredox catalysis
Physical Sciences
Quinones
Science & Technology
Sodium
ALKENES
1,6-CONJUGATE ADDITION
ALKYL RADICALS
FLUOROALKYLATION
ISOCYANIDES
CATALYZED TRIFLUOROMETHYLATION
ORGANOFLUORINE CHEMISTRY
RADICAL-ADDITION REACTIONS
CYCLIZATION
PHOTOREDOX CATALYSIS
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Summary:The radical tri-/difluoromethylation of para-quinone methides with readily available sodium tri-/difluoromethanesulfinate via organic photoredox catalysis is described. This reaction is external oxidant free and exhibits wide functional group compatibility, providing the desired products in useful yields. However, the reaction of para-quinone methides with CH2FSO2Na and CH3SO2Na under the optimal conditions gives the nucleophilic conjugate addition products. The results indicate that the strong inductive effect of the fluorine atom may play a critical role in the reactivity of the sodium sulfinates.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c8qo00428e