Base-Promoted Annulative Difluoromethylenation of Enaminones with BrCF₂CO₂Et toward 2,2-Difluorinated 2,3-Dihydrofurans

Jinbiao Ying, Ting Liu, Yunyun Liu* and Jie-Ping Wan*

*College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. China, Email: chemliuyunyunjxnu.edu.cn, wanjiepingjxnu.edu.cn

J. Ying, T. Liu, Y. Liu, J.-P. Wan, Org. Lett., 2022, 24, 2393-2398.

DOI: 10.1021/acs.orglett.2c00671

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Abstract

A [4 + 1] annulation of enaminones and BrCF₂CO₂Et enables a practical synthesis of 2,2-difluorinated 2,3-dihydrofurans in the presence of Na₂CO₃. A subsequent reaction with hydrochloric acid provides β-keto enoic acids (4-oxo-2-butenoic acids).

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proposed mechanism

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Key Words

2,3-Dihydrofurans

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ID: J54-Y2022