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Rohde, Jan-Uwe
Transition Metal Chemistry
Research Interests
  • Inorganic chemistry, coordination chemistry, organometallic chemistry, chemical synthesis, catalysis, green chemistry, inorganic reaction mechanisms.

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Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability

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Title
Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability
Author
Maiti, SaikatKim, JaeshinPark, Jae-HeonNam, DongsikLee, Jae BinKim, Ye JinKee, Jung-MinSeo, Jeong KonMyung, KyungjaeRohde, Jan-UweChoe, WonyoungKwon, Oh HoonHong, Sung You
Issue Date
2019-06
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF ORGANIC CHEMISTRY, v.84, no.11, pp.6737 - 6751
Abstract
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.
URI
https://scholarworks.unist.ac.kr/handle/201301/26874
URL
https://pubs.acs.org/doi/10.1021/acs.joc.9b00470
DOI
10.1021/acs.joc.9b00470
ISSN
0022-3263
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