Li Jian, Liu Junjie, Yin Jiangliang, Zhang Yuming, Han Weiguo, Lan Jingbo, Wu Di, Bin Zhengyang, You Jingsong
Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry , Sichuan University , 29 Wangjiang Road , Chengdu 610064 , People's Republic of China.
J Org Chem. 2019 Dec 6;84(23):15697-15705. doi: 10.1021/acs.joc.9b02339. Epub 2019 Nov 8.
It remains a challenge to achieve ,-double annulations of primary benzamides with aryl alkynes due to competitive ,-double annulations. Herein, we employed sterically hindered 1-methylcyclohexane-1-carboxylic acid to address this challenge, the double -C-H activation of benzamides and subsequent ,-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.
