EDA Complex Initiated C-H Difluoroalkylation of Quinoxalin-2(1H)-ones with Fluoroalkyl Bromides
Huanhuan Cui1, Chunyu Hu1, Xiulin Qiao1
1College of Chemistry, Chemical Engineering and Material Science, Zaozhuang University, Zaozhuang, Shandong 277160, P. R. China.
Abstract:
An efficient visible-light-induced EDA strategy has been developed for constructing 3-difluoroalkylated quinoxalin-2(1H)-ones through the C-H difluoroalkylation of quinoxalin-2(1H)-ones with fluoroalkyl bromides. This transformation could provide a series of 3-difluoroalkylated quinoxalin-2(1H)-ones in moderate to good yields under mild and metal-free conditions. Mechanistic studies revealed that the formation of the EDA complex between fluoroalkyl bromide and TMEDA was essential to initiate this transformation.
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Nucleophilic Aromatic Substitution: Elimination–Addition
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Radical Substitution: Allylic Bromination


