American Chemical Society
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Double ortho-C–H Activation/Annulation of Benzamides with Aryl Alkynes: A Route to Double-Helical Polycyclic Heteroaromatics

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posted on 2019-11-08, 18:03 authored by Jian Li, Junjie Liu, Jiangliang Yin, Yuming Zhang, Weiguo Han, Jingbo Lan, Di Wu, Zhengyang Bin, Jingsong You
It remains a challenge to achieve N,O-double annulations of primary benzamides with aryl alkynes due to competitive N,N-double annulations. Herein, we employed sterically hindered 1-methylcyclohexane-1-carboxylic acid to address this challenge, the double ortho-C–H activation of benzamides and subsequent N,O-double annulations with aryl alkynes have been accomplished for the first time. The resulting product can be further transformed into a double-helical extended π-conjugated polycyclic heteroarene via Scholl oxidation, which exhibits blue emission with high fluorescence quantum yields.