3-Trifluoromethyl Pyrrole Synthesis Based on β-CF3-1,3-Enynamides,The Journal of Organic Chemistry

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3-Trifluoromethyl Pyrrole Synthesis Based on β-CF3-1,3-Enynamides
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-10-18 , DOI: 10.1021/acs.joc.3c01790
Zongxiang Yu ₁ , Jintong Li ₁ , Yuxuan Cao ₁ , Tingwei Dong ₁ , Yuanjing Xiao ₁

Affiliation

A new metal-free method for the rapid, productive, and scalable preparation of 3-trifluoromethyl pyrroles has been developed. It is based on the electrophilic nature of the double bond of β-CF₃-1,3-enynamides due to the electron-withdrawing characteristics of the trifluoromethyl groups and the strong nucleophilic nature of alkyl primary amines. Evidence for the highly regioselective 1,4-hydroamination was observed after the isolation and characterization of the allenamide intermediate.

中文翻译：

基于β-CF3-1,3-烯炔酰胺的3-三氟甲基吡咯合成

开发了一种快速、高效且可规模化制备 3-三氟甲基吡咯的新无金属方法。它基于由于三氟甲基的吸电子特性和烷基伯胺的强亲核特性而导致的β-CF _{3 -1,3-烯酰胺双键的亲电特性。}在分离和表征丙二烯酰胺中间体后，观察到了高度区域选择性 1,4-氢胺化的证据。

更新日期：2023-10-18

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