title: Photocatalyzed benzylic fluorination: shedding "light" on the involvement of electron transfer.
abstract: The photocatalyzed oxidation of benzylic compounds by 1,2,4,5-tetracyanobenzene (TCB) in the presence of Selectfluor provides a synthetically efficient route to electron deficient, less substituted, and otherwise inaccessible benzylic fluorides. The virtue of this system is multifold: it is metal-free and mild, and the reagents are inexpensive. Mechanistically, the data suggest the intimate formation of intermediate radical cations in the key radical forming step, as opposed to a concerted hydrogen atom transfer process.
authors.affiliation: Contribution from the Department of Chemistry, New Chemistry Building, Johns Hopkins University , 3400 North Charles Street, Baltimore, Maryland 21218, United States.
authors.forename: Steven
authors.initials: S
authors.lastname: Bloom
authors.forename: Michael
authors.initials: M
authors.lastname: McCann
authors.forename: Thomas
authors.initials: T
authors.lastname: Lectka