Scheme 3. Benzylic C–H Cross-Coupling to C–O, C–N, and C–C Bonds via a Benzyl Fluoride.

^aReaction uses 10 equiv HFIP as a H-bond donor. Isolated yields calculated with respect to the ¹H NMR yield of the benzyl fluoride (or the C–H substrate, in parentheses). ^b10 mol% BF₃•Et₂O used instead of HFIP. ^c50 mol% BF₃•Et₂O used instead of HFIP ^dBoth HFIP and BF₃•Et₂O used. ^e2.5 equiv MsOH added to the nucleophile. ^fUsed dichloromethane as the fluorination reaction solvent. ^g1.5 equiv BF₃•Et₂O used instead of HFIP. Isolated as the amine.