A facile 2, 2, 2-trifluoroethyl fatty acid ester synthesis with phenyl(2, 2, 2-trifluoroethyl)iodonium triflate at room temperature. Issue 3 (3rd July 2017)

• Record Type: Journal Article
• Authors: Han, Qiu-Yan; Zhao, Cheng-Long; Yang, Jing; Zhang, Cheng-Pan
• Is Part Of: Green chemistry letters and reviews. Volume 10:Issue 3(2017)
• Page Start: 162
• Page End: 170
• Publication Date: 2017-07-03
• Subjects: 2, 2, 2-trifluoroethyl -- fatty acids -- esters -- phenyl(2, 2, 2-trifluoroethyl)iodonium; Green chemistry -- Periodicals; 540
• DOI: 10.1080/17518253.2017.1338759
• Languages: English
• ISSNs: 1751-8253

Abstract

ABSTRACT: A series of complex 2, 2, 2-trifluoroethyl fatty acid esters were synthesized by the reaction of fatty acids and phenyl(2, 2, 2-trifluoroethyl)iodonium triflate in the presence of Cs2 CO3 . The reaction at room temperature without any other additive provided the corresponding 2, 2, 2-trifluoroethyl esters in up to quantitative yield. The conjugated carbon–carbon double bonds, the unprotected hydroxyl group, and the amido functionalities in the substrates are all tolerated in the reaction. Compared to the known synthetic methods, advantages of this reaction include mild conditions, good functional group tolerance, and without using harsh and toxic condensation agents, which allows for a green, facile, and efficient way to 2, 2, 2-trifluoroethyl fatty acid esters. GRAPHICAL ABSTRACT: