Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability
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- Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability
- Maiti, Saikat; Kim, Jaeshin; Park, Jae-Heon; Nam, Dongsik; Lee, Jae Bin; Kim, Ye Jin; Kee, Jung-Min; Seo, Jeong Kon; Myung, Kyungjae; Rohde, Jan-Uwe; Choe, Wonyoung; Kwon, Oh Hoon; Hong, Sung You
- Issue Date
- AMER CHEMICAL SOC
- JOURNAL OF ORGANIC CHEMISTRY, v.84, no.11, pp.6737 - 6751
- 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.
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