Visible Light-Promoted Aromatization-Driven Deconstructive Fluorination of Spiro Carbocycles

Org Lett. 2024 Sep 6;26(35):7442-7446. doi: 10.1021/acs.orglett.4c02793. Epub 2024 Aug 26.

Abstract

A visible light-promoted aromatization-driven deconstructive fluorination of spiro carbocycles is presented. A series of spiro dihydroquinazolinones reacted efficiently with NFSI under visible light irradiation to afford the 2-(4-fluoroalkyl)quinazolin-4(3H)-ones in good yields with excellent functional group tolerance. A radical pathway involving C-C bond cleavage and F atom transfer is proposed for the reaction. In addition, the ring-opening chlorination of spiro dihydroquinazolinones with NCS was also applicable.