Visible-Light-Promoted Dearomative Fluoroalkylation of beta-Naphthols through Intermolecular Charge Transfer

The first visible-light-promoted dearomative fluoroalkylation of beta-naphthols was realized without the assistance of any transition-metal catalysts or external photosensitizers. Inexpensive fluoroalkyl iodides were directly used as efficient fluoroalkylation reagents under very mild reaction conditions. The scope of this process was found to be general and broad, and both trifluoromethyl and perfluoroalkyl groups (-C4F9, -C6F13, and -C8F17) were installed in excellent yields. Preliminary mechanistic studies suggest that visible-light-promoted intermolecular charge transfer within the naphtholate-fluoroalkyl iodide electron donor-acceptor (EDA) complex induces a single electron transfer in the absence of photocatalysts.