Diazotrifluoroethyl Radical: A CF3-Containing Building Block in [3 + 2] Cycloaddition

Autor: Nan-Wei Wan, Wenyong Han, Chun-Yang He, Yongzheng Chen, Yong-Chao Shao, Jia-Li Huang, Baodong Cui, An-Ni Wang, Wen-Wen Zhao
Rok vydání: 2021
Předmět:
Zdroj: Organic Letters. 23:9256-9261
ISSN: 1523-7052
1523-7060
DOI: 10.1021/acs.orglett.1c03603
Popis: We present herein a visible-light-induced [3 + 2] cycloaddition of a hypervalent iodine(III) reagent with α-ketoacids for the construction of 5-CF3-1,3,4-oxadiazoles that are of importance in medicinal chemistry. The reaction proceeds smoothly without a photocatalyst, metal, or additive under mild conditions. Different from the well-established trifluorodiazoethane (CF3CHN2), the diazotrifluoroethyl radical [CF3C(·)N2], a trifluoroethylcarbyne (CF3CĊ:) equivalent and an unusual CF3-containing building block, is involved in the present reaction system.
Databáze: OpenAIRE