posted on 2019-05-03, 00:00authored bySaikat Maiti, Jaeshin Kim, Jae-Heon Park, Dongsik Nam, Jae Bin Lee, Ye-Jin Kim, Jung-Min Kee, Jeong Kon Seo, Kyungjae Myung, Jan-Uwe Rohde, Wonyoung Choe, Oh-Hoon Kwon, Sung You Hong
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.