San Htet Htet, Wang Chun-Ying, Zeng Hai-Peng, Fu Shi-Tao, Jiang Min, Tang Xiang-Ying
School of Chemistry and Chemical Engineering and Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica , Huazhong University of Science and Technology , 1037 Luoyu Road , Wuhan 430074 , People's Republic of China.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry (SIOC) , Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , People's Republic of China.
J Org Chem. 2019 Apr 5;84(7):4478-4485. doi: 10.1021/acs.joc.8b03278. Epub 2019 Mar 19.
A challenging metal-free azide insertion of α-aryl α-diazoesters in the presence of B(CF) (5 mol %) was developed for the first time. The reaction features an easy operation, wide substrate scope, and mild conditions and affords the corresponding products in moderate to high yields. More importantly, alkene and alkyne functional groups were well tolerated because no cyclopropanation or cyclopropenation was observed. Furthermore, the corresponding azide products could be converted to primary amines or 1,2,3-triazole derivatives after simple transformations.
