Oxidation of difluorocarbene and subsequent trifluoromethoxylation

Jiao Yu; Jin-Hong Lin; Donghai Yu; Ruobing Du; Ji-Chang Xiao

doi:10.1038/s41467-019-13359-z

Oxidation of difluorocarbene and subsequent trifluoromethoxylation

Nat Commun. 2019 Nov 25;10(1):5362. doi: 10.1038/s41467-019-13359-z.

Authors

Jiao Yu¹, Jin-Hong Lin¹, Donghai Yu¹, Ruobing Du¹, Ji-Chang Xiao²

Affiliations

¹ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, 200032, Shanghai, China.
² Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, 200032, Shanghai, China. jchxiao@sioc.ac.cn.

Abstract

As a versatile intermediate, difluorocarbene is an electron-deficient transient species, meaning that its oxidation would be challenging. Herein we show that the oxidation of difluorocarbene could occur smoothly to generate carbonyl fluoride. The oxidation process is confirmed by successful trifluoromethoxylation, ¹⁸O-trifluoromethoxylation, the observation of AgOCF₃ species, and DFT calculations.

Publication types

Research Support, Non-U.S. Gov't