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Copper-Catalyzed C–H Oxidative Radical Functionalization and Annulation of Aniline-Linked 1,7-Enynes: Evidence for a 1,5-Hydride Shift Mechanism

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journal contribution
posted on 06.12.2016 by Ming Hu, Hua-Xu Zou, Ren-Jie Song, Jian-Nan Xiang, Jin-Heng Li
A new copper-catalyzed tandem C–H oxidative radical functionalization and annulation of aniline-linked 1,7-enynes with alkyl nitriles or acetone is described. This reaction allows the selective construction of 1H-cyclopenta­[c]­quinolines and benzo­[j]­phenanthridin-6­(5H)-ones which rely on the substitution effect at the 2-position of the acrylamide moiety. The mechanism involving a 1,5-hydride shift process is proposed according to the control deuterium-labeled experiment.