Scheme 3.

Proposed mechanism (A) and Derivatization Reactions (B)

(A) Proposed mechanism for the preparation of fluorinated benzyl bromides 3. (B) Derivatization reactions. Reaction conditions: i) 1 (0.5 mmol), 2a (1.0 mmol), Ir(ppy)₃ (0.1 mol %) in MeCN (5.0 mL, 0.1 M), 24 h irradiation with blue LED strips (λ_max = 456 nm). ii) Filtration through a short pad of silica. iii) NaN₃ (0.75 mmol) in DMSO (5 mL, 0.1 M), overnight at rt. iv) EtONa (2.5 mmol) in EtOH (5 mL, 0.1 M), overnight at rt. v) AgOAc (0.5 mmol) in MeCN, 4 h at 50 °C. ^aIsolated yield from 1a.