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

作者:Yu, Zongxiang; Li, Jintong; Cao, Yuxuan; Dong, Tingwei; Xiao, Yuanjing*
来源:Journal of Organic Chemistry, 2023, 88(21): 15501-15506.
DOI:10.1021/acs.joc.3c01790

摘要

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 beta-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.

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