A novel and efficient electrochemical method for electroselective and controlled cross-coupling of isoindolinones with equivalent alcohols has been developed without the need for metal catalysts and strong bases under mild conditions. The reaction provides a novel strategy for the controllable and effective synthesis of 3-alkoxyl and -hydroxymethyl-substituted isoindolinones, which is adjusted by 4-OH-TEMPO and tolerates various substrates. This protocol is an efficient tool for the construction of C-O and C-N bonds with high chemoselectivity.
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http://dx.doi.org/10.1021/acs.joc.4c02838 | DOI Listing |
J Org Chem
January 2025
The Center for Combinatorial Chemistry and Drug Discovery of Jilin University, The School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Road, Changchun, Jilin 130021, P. R. China.
A novel and efficient electrochemical method for electroselective and controlled cross-coupling of isoindolinones with equivalent alcohols has been developed without the need for metal catalysts and strong bases under mild conditions. The reaction provides a novel strategy for the controllable and effective synthesis of 3-alkoxyl and -hydroxymethyl-substituted isoindolinones, which is adjusted by 4-OH-TEMPO and tolerates various substrates. This protocol is an efficient tool for the construction of C-O and C-N bonds with high chemoselectivity.
View Article and Find Full Text PDFOrg Lett
March 2021
The Center for Combinatorial Chemistry and Drug Discovery of Jilin University, The School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Road, Changchun, Jilin 130021, P. R. China.
An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.
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