Visible-Light-Induced Secondary Benzylic C(sp3)-H Functionalization for Nucleophilic Substitution: An Intermolecular C-X (C-N, C-C, and C-Br) Bond Forming Reaction

Abstract

Exploring new synthetic methods that harness visible light represents a breakthrough in organic synthesis. Amides, amines, nitriles, and halides are essential functional groups and serve as key building blocks in the synthesis of complex molecules in organic and medicinal chemistry. This study introduces a novel intermolecular benzylic C-X (C-N, C-C, and C-Br) bond formation via photoredox benzylic C(sp3)-H bonds. This methodology enables the synthesis of secondary amides, nitriles, and halides through reacting secondary benzylic substrates with readily accessible reagents including BocNH<inf>2</inf>, benzamide, acetamide, TMSCN, and TBAB. This approach displays the potential of being sustainable and efficient to afford amidation, cyanation, and halogenation products in good yields. © 2025 American Chemical Society.