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室温下三级卤代烷烃的选择性氟代反应。

Selective Radical Fluorination of Tertiary Alkyl Halides at Room Temperature.

机构信息

Key Laboratory of Organofluorine Chemistry and Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.

AnHui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Anhui University, Hefei, Anhui, 230601, P. R. China.

出版信息

Angew Chem Int Ed Engl. 2017 Nov 27;56(48):15411-15415. doi: 10.1002/anie.201708197. Epub 2017 Nov 2.

Abstract

Direct fluorination of tertiary alkyl bromides and iodides with Selectfluor is described. The halogen-exchange fluorination proceeds efficiently in acetonitrile at room temperature under metal-free conditions and exhibits a wide range of functional group compatibility. Furthermore, the reactions are highly selective in that alkyl chlorides and primary and secondary alkyl bromides remain intact. A radical mechanism is proposed for this selective fluorination.

摘要

本文描述了用 Selectfluor 对三级烷基溴化物和碘化物的直接氟化反应。在无金属条件下,卤素交换氟化反应在乙腈中于室温下高效进行,并且具有广泛的官能团兼容性。此外,这些反应具有高度的选择性,因为烷基氯化物和伯、仲烷基溴化物保持不变。为这种选择性氟化反应提出了自由基机理。

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