Abstract
The NHC (NHC = N-heterocyclic carbene) complex Cp*(IPr)RuH3 catalyzes hydrodefluorination of aromatic fluorides at 70 °C with isopropyl alcohol as the reducing reagent. The reaction is selective for aromatic fluorides, as almost negligible C(sp3)–F bond reduction takes place. The activity decreases from more to less fluorinated substrates, but polyaromatic monofluorides, such as 1-fluoronaphthalene and 6-fluoro-2-methylquinoline, can also be reduced in moderate to good yields. Kinetic studies are consistent with a mechanism based on elimination of NHC and reversible substrate coordination, followed by coordination of the alcohol.
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