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Issue 13, 2018
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Redox-neutral tri-/difluoromethylation of para-quinone methides with sodium sulfinates

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Abstract

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.

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

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Publication details

The article was received on 27 Apr 2018, accepted on 15 May 2018 and first published on 17 May 2018


Article type: Research Article
DOI: 10.1039/C8QO00428E
Citation: Org. Chem. Front., 2018,5, 2061-2064
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    Redox-neutral tri-/difluoromethylation of para-quinone methides with sodium sulfinates

    Q. Wu, G. Ao and F. Liu, Org. Chem. Front., 2018, 5, 2061
    DOI: 10.1039/C8QO00428E

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