Site-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.
Site-selective transformation of benzylicn class="Chemical">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.
Authors: Matthew B Nodwell; Abhimanyu Bagai; Shira D Halperin; Rainer E Martin; Henner Knust; Robert Britton Journal: Chem Commun (Camb) Date: 2015-07-28 Impact factor: 6.222
Authors: Robert Szpera; Daniel F J Moseley; Lewis B Smith; Alistair J Sterling; Véronique Gouverneur Journal: Angew Chem Int Ed Engl Date: 2019-08-20 Impact factor: 15.336