Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability

Herein,
we report chemoselective trifluoroethylation routes of
unmasked 2-arylquinazolin-4­(3H)-ones using mesityl­(2,2,2-trifluoroethyl)­iodonium
triflate at room temperature. Homologous C-, O-, and N-functionalized
subclasses are accessed in a straightforward manner with a wide substrate
scope. These chemoselective branching events are driven by Pd-catalyzed
ortho-selective C–H activation at the pendant aryl ring and
base-promoted reactivity modulation of the amide group, leveraging
the intrinsic directing capability and competing pronucleophilicity
of the quinazolin-4­(3H)-one framework. Furthermore,
outstanding photostability of the quinazolin-4­(3H)-one family associated with nonradiative decay is presented.