Synthesis of trans-2-(Disubstituted-amino)alkenyl Polyoxyperfluoroalkyl Ketones from Tertiary Amines and Perfluoroalkyl Ether Carboxylates Featuring “–CF2O–” Units

Qin-Yuan Ni; Shiyu Zhao; Chengying Wu; Yong Guo; Ji-Chang Xiao

doi:10.1002/cjoc.70055

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (15) : 1847 -1854. DOI: 10.1002/cjoc.70055

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Synthesis of trans-2-(Disubstituted-amino)alkenyl Polyoxyperfluoroalkyl Ketones from Tertiary Amines and Perfluoroalkyl Ether Carboxylates Featuring “–CF₂O–” Units

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Abstract

A one-pot transformation of aliphatic and aromatic tertiary amines to novel fluorinated enaminones has been developed, utilizing perfluoroalkyl ether carboxylates (PFECA salts) featuring “–CF₂O–” units as the fluorine-containing reagents. Carbonyl fluoride, acyl fluorides and anhydrides by thermal decomposition of these PFECA salts were proposed to act as key active species that trigger the tandem oxidation–acylation process of tertiary amines, through enamine intermediates.

Keywords

Fluorine / Oxidation / Acylation / Perfluoroalkyl ether carboxylates / Tertiary amines / Enaminones

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Qin-Yuan Ni, Shiyu Zhao, Chengying Wu, Yong Guo, Ji-Chang Xiao. Synthesis of trans-2-(Disubstituted-amino)alkenyl Polyoxyperfluoroalkyl Ketones from Tertiary Amines and Perfluoroalkyl Ether Carboxylates Featuring “–CF₂O–” Units. Chinese Journal of Chemistry, 2025, 43(15): 1847-1854 DOI:10.1002/cjoc.70055