3‑Trifluoromethyl Pyrrole Synthesis Based on β‑CF3‑1,3-Enynamides

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 stron...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-11, Vol.88 (21), p.15501-15506
Main Authors: Yu, Zongxiang, Li, Jintong, Cao, Yuxuan, Dong, Tingwei, Xiao, Yuanjing
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01790