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Radical C(sp2)-H Trifluoromethylation of Aldehydes in Aqueous Solution

Pei Zhang, Haigen Shen, Lin Zhu*, Weiguo Cao*, Chaozhong Li*

*SIOC, 345 Lingling Road, Shanghai 200032; Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, China, Email: zhulinmail.ustc.edu.cn, wgcaostaff.shu.edu.cn, cligmail.sioc.ac.cn

P. Zhang, H. Shen, L. Zhu, W. Cao, C. Li, Org. Lett., 2018, 20, 7062-7065.

DOI: 10.1021/acs.orglett.8b03012


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Abstract

The trifluoromethylation of aldehydes with (bpy)Cu(CF3)3, Et3SiH, and K2S2O8 in aqueous acetone at room temperature provides the corresponding trifluoromethyl ketones in satisfactory yields. The protocol is applicable to both aliphatic and aromatic aldehydes and exhibits wide functional group compatibility. A mechanism involving Cu(II)-mediated trifluoromethylation of acyl radicals is proposed.


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proposed mechanism



Key Words

trifluoromethyl ketones, potassium peroxydisulfate


ID: J54-Y2018