American Chemical Society
jo9b00470_si_004.cif (3.06 MB)

Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability

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posted on 2019-05-03, 00:00 authored by Saikat 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.