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

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...

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Veröffentlicht in:	Organic letters 2021-12, Vol.23 (23), p.9256-9261
Hauptverfasser:	Zhao, Wen-Wen, Shao, Yong-Chao, Wang, An-Ni, Huang, Jia-Li, He, Chun-Yang, Cui, Bao-Dong, Wan, Nan-Wei, Chen, Yong-Zheng, Han, Wen-Yong
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container_issue	23
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container_title	Organic letters
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creator	Zhao, Wen-Wen Shao, Yong-Chao Wang, An-Ni Huang, Jia-Li He, Chun-Yang Cui, Bao-Dong Wan, Nan-Wei Chen, Yong-Zheng Han, Wen-Yong
description	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.
doi_str_mv	10.1021/acs.orglett.1c03603
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title	Diazotrifluoroethyl Radical: A CF3‑Containing Building Block in [3 + 2] Cycloaddition
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