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Computational and experimental studies on copper-mediated selective cascade C–H/N–H annulation of electron-deficient acrylamide with arynes

Chen, Chao, Hao, Yu, Zhang, Ting-Yu, Pan, Jin-Long, Ding, Jun, Xiang, Heng-Ye, Wang, Man, Ding, Tong-Mei, Duan, Abing, Zhang, Shu-Yu
Chemical communications 2019 v.55 no.6 pp. 755-758
acrylamides, carbon-hydrogen bond activation, chemical bonding, chemical reactions, copper, density functional theory, moieties
An efficient and convenient copper-mediated method has been developed to achieve direct cascade C–H/N–H annulation to synthesize 2-quinolinones from electron-deficient acrylamides and arynes. This method highlights an emerging but simple strategy to transform inert C–H bonds into versatile functional groups in organic synthesis to provide a new method of synthesizing 2-quinolinones efficiently. Mechanistic investigations by experimental and density functional theory (DFT) studies suggest that an organometallic C–H activation via a Cu(iii) intermediate is likely to be involved in the reaction.