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• W3026491163 endingPage "8141" @default.
• W3026491163 startingPage "8121" @default.
• W3026491163 abstract "This article describes the identification of 1-(2-hydroxyethyl)-piperazine as a new, cost-effective, highly efficient organocatalyst, which promotes both inter- and intra-molecular direct C(sp2)–H arylations of unactivated arenes in the presence of potassium tert-butoxide. While the inter-molecular C–H arylation of unactivated benzenes with aryl halides (Ar–X; X = I, Br, Cl) toward biaryl syntheses underwent smoothly in the presence of only 10 mol % organocatalyst, the intra-molecular C–H arylation catalytic system composed of 40 mol % each of the catalyst and the additive (4-dimethylaminopyridine (DMAP)). The novel catalyst was also able to perform both inter- and intra-molecular direct arylations simultaneously in a single pot. The mechanistic studies confirmed the involvement of aryl radical anions and proceeded via a single-electron-transfer (SET) mechanism. The large substrate scope, high functional group tolerance, competition experiments, gram-scale synthesis, and kinetic studies further highlight the importance and versatile nature of the methodology as well as the compatibility of the new catalyst. To the best of our knowledge, this is the first report on any organocatalyst that reported detailed investigations of both inter- and intra-molecular direct C(sp2)–H arylations of unactivated arenes in a single representation." @default.
• W3026491163 created "2020-05-29" @default.
• W3026491163 creator A5007457714 @default.
• W3026491163 creator A5010041569 @default.
• W3026491163 creator A5057161121 @default.
• W3026491163 creator A5072426581 @default.
• W3026491163 date "2020-05-22" @default.
• W3026491163 modified "2023-10-14" @default.
• W3026491163 title "Organocatalyst in Direct C(_sp²)–H Arylation of Unactivated Arenes: [1-(2-Hydroxyethyl)-piperazine]-Catalyzed <i>Inter</i>-/<i>Intra</i>-molecular C–H Bond Activation" @default.
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• W3026491163 doi "https://doi.org/10.1021/acs.joc.0c01019" @default.
• W3026491163 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/32438807" @default.
• W3026491163 hasPublicationYear "2020" @default.
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