ol0c02238_si_001.pdf (9.7 MB)
Copper-Catalyzed C–H Fluorination/Functionalization Sequence Enabling Benzylic C–H Cross Coupling with Diverse Nucleophiles
journal contribution
posted on 2020-07-29, 18:05 authored by Aristidis Vasilopoulos, Dung L. Golden, Joshua A. Buss, Shannon S. StahlSite-selective transformation
of benzylic C–H bonds into
diverse functional groups is achieved via Cu-catalyzed C–H
fluorination with N-fluorobenzenesulfonimide (NFSI),
followed by substitution of the resulting fluoride with various nucleophiles.
The benzyl fluorides generated in these reactions are reactive electrophiles
in the presence of hydrogen-bond donors or Lewis acids, allowing them
to be used without isolation in C–O, C–N, and C–C
coupling reactions.