Synthetic Approaches to Trifluoromethoxy‐Substituted Compounds

Abstract

Because of the unique properties of the trifluoromethoxy group, molecules bearing this moiety will find applications in various fields, particularly in the life sciences. However, despite the great interest in this functional group, only a small number of trifluoromethoxylated molecules are currently synthetically accessible. Over the last few years, several innovative and promising strategies for the synthesis of trifluoromethoxylated compounds have been described. This Minireview discusses these existing methods with a particular focus on more recent advances.

Merging Visible‐Light Catalysis for the Direct Late‐Stage Group‐16–Trifluoromethyl Bond Formation

“…The SCF 3 group is by far the most studied motif in the series of trifluoromethylchalcogen groups, probably due to the presence of different sources of SCF 3 , electrophilic, nucleophilic as well as radical sources –. In addition to the developed methodologies, the use of photoredox catalysis emerged recently to complement the toolbox .…”

Targeted Fluoro Positioning for the Discovery of a Potent and Highly Selective Matrix Metalloproteinase Inhibitor

“…Fluorine‐containing compounds have gained emerging interest in chemistry, as synthetic strategies have evolved to allow the diverse use of this formerly exotic element . Owing to its small size, with a van der Waals radius of 1.47 Å (in comparison to 1.20 Å for hydrogen and 1.52 Å for oxygen), and its high electronegativity (3.98 according to the Pauling scale in contrast to 2.20 for hydrogen), fluorine can be incorporated into molecules to substitute a hydrogen atom and to alter the physicochemical properties without applying major changes to the size of the compound .…”

Visible‐Light Photoredox‐Catalyzed and Copper‐Promoted Trifluoromethoxylation of Arenediazonium Tetrafluoroborates

“…[1] Therefore,t he development of new methods for the synthesis of trifluoromethyl ethers has received much attention. [3] Herein, we reported the first example of ap hotoredox-catalyzed and copper-promoted trifluoromethoxylation of arenediazonium tetrafluoroborates under mild reaction conditions,w ith trifluoromethyl arylsulfonate (TFMS,2) [4] as the trifluoromethoxylation reagent (Scheme 1). [3] Herein, we reported the first example of ap hotoredox-catalyzed and copper-promoted trifluoromethoxylation of arenediazonium tetrafluoroborates under mild reaction conditions,w ith trifluoromethyl arylsulfonate (TFMS,2) [4] as the trifluoromethoxylation reagent (Scheme 1).…”