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• W2317509225 endingPage "2954" @default.
• W2317509225 startingPage "2944" @default.
• W2317509225 abstract "A new reaction for the synthesis of dimethylisoindolinones has been presented from 2-halo-N-isopropyl-N-alkylbenzamide substrates and KOtBu by the selective C–C coupling of an unreactive tertiary sp3 C–H bond. The reaction manifested an excellent selectivity toward a tertiary sp3 C–H bond over primary or sec C–H bond. Moreover, biaryl C–C coupling along with alkyl–aryl C–C coupling can be achieved in one pot using dihalobenzamides for the synthesis of biaryl 5-phenylisoindolin-1-ones. It seems that the reaction proceeds via a radical pathway in which the aryl radical translocates via 1,5-hydrogen atom transfer (HAT), forming a tertiary alkyl carbon-centered radical. The generated tertiary alkyl radical could attack the benzamide ring in a 5-exo/endo-trig manner followed by the release of an electron and a proton, leading to a five-membered isoindolinone ring. HAT seems to be responsible for the selective functionalization of the tertiary alkyl group over primary and secondary C–H bonds." @default.
• W2317509225 created "2016-06-24" @default.
• W2317509225 creator A5028684932 @default.
• W2317509225 creator A5036729888 @default.
• W2317509225 creator A5037474329 @default.
• W2317509225 creator A5041944543 @default.
• W2317509225 creator A5055058819 @default.
• W2317509225 creator A5087231410 @default.
• W2317509225 date "2014-03-17" @default.
• W2317509225 modified "2023-10-10" @default.
• W2317509225 title "KO^<i>t</i>Bu-Mediated Synthesis of Dimethylisoindolin-1-ones and Dimethyl-5-phenylisoindolin-1-ones: Selective C–C Coupling of an Unreactive Tertiary sp³ C–H Bond" @default.
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• W2317509225 doi "https://doi.org/10.1021/jo402776u" @default.
• W2317509225 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24597670" @default.
• W2317509225 hasPublicationYear "2014" @default.
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