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

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Diazotrifluoroethyl Radical: A CF3-Containing Building Block in [3 + 2] Cycloaddition
Organic Letters ( IF 4.9 ) Pub Date : 2021-11-21 , DOI: 10.1021/acs.orglett.1c03603
Wen-Wen Zhao ₁ , Yong-Chao Shao ₁ , An-Ni Wang ₁ , Jia-Li Huang ₁ , 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}

Affiliation

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.

中文翻译：

重氮三氟乙基自由基：[3 + 2] 环加成中的含 CF3 结构单元

我们在此展示了一种高价碘 (III) 试剂与 α-酮酸的可见光诱导 [3 + 2] 环加成，用于构建在药物化学中具有重要意义的 5-CF ₃ -1,3,4-恶二唑. 反应在温和条件下顺利进行，无需光催化剂、金属或添加剂。与成熟的三氟重氮乙烷 (CF ₃ CHN ₂ ) 不同，重氮三氟乙基自由基 [CF ₃ C(·)N ₂ ] 是一种三氟乙炔 (CF ₃ CĊ:) 等效物，是一种不常见的含 CF ₃的结构单元。目前的反应体系。

更新日期：2021-12-03

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