| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1313470 | Journal of Fluorine Chemistry | 2016 | 6 Pages |
•The addition of trifluoroacetic acid drastically reduces the induction period.•Lower reaction temperature is enabled.•Milder conditions for benzylic fluorides bearing an electron-withdrawing group.
We report that the addition of a catalytic amount of trifluoroacetic acid (TFA) shortens the induction period associated with the 1,1,1,3,3,3-hexafluoroisopropoanol (HFIP)-promoted Friedel-Crafts reaction of benzylic fluorides. This faster initiation is due to TFA’s strong hydrogen-bond donation capability, not its Brønsted acidity. The improved reaction conditions were applied to a set of substrates, demonstrating how they could improve yields and reliability of this transformation.
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