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

Wen-Wen Zhao; Yong-Chao Shao; An-Ni Wang; Jia-Li Huang; Chun-Yang He; Bao-Dong Cui; Nan-Wei Wan; Yong-Zheng Chen; Wen-Yong Han

doi:10.1021/acs.orglett.1c03603

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

Org Lett. 2021 Dec 3;23(23):9256-9261. doi: 10.1021/acs.orglett.1c03603. Epub 2021 Nov 21.

Authors

Wen-Wen Zhao¹, Yong-Chao Shao¹, An-Ni Wang¹, Jia-Li Huang¹, Chun-Yang He^{1

2}, Bao-Dong Cui^{1

2}, Nan-Wei Wan^{1

2}, Yong-Zheng Chen^{1

2}, Wen-Yong Han^{1

2}

Affiliations

¹ Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, Green Pharmaceuticals Engineering Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi 563006, P. R. China.
² Key Laboratory of Basic Pharmacology of Ministry of Education and Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi 563006, P. R. China.

PMID: 34802247
DOI: 10.1021/acs.orglett.1c03603

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't