52771-22-9

Usage

Chemical Properties

CLEAR VERY SLIGHTLY YELLOW LIQUID

InChI:InChI=1/C8H4F3NO/c9-8(10,11)13-7-3-1-2-6(4-7)5-12/h1-4H

Upstream product

• 93071-75-1 1-[3-(trifluoromethoxy)phenyl]methanamine 
• 100-47-0 benzonitrile 
• 57830-55-4 2-((trifluoromethyl)sulfonyl)pyridine 
• 1006904-72-8 silver(I) trifluoromethoxide 
• 2237-30-1 m-cyanoaniline 
• 2252-44-0 1-bromo-3-(trifluoromethoxy)benzene 
• 927-84-4 bis(trifluoromethyl)peroxide 

Downstream Products

• 886500-80-7 N'-hydroxy-3-(trifluoromethoxy)benzenecarboximidamide 
• 93071-75-1 1-[3-(trifluoromethoxy)phenyl]methanamine 

Relevant academic research and scientific papers

Electrochemical Trifluoromethoxylation of (Hetero)aromatics with a Trifluoromethyl Source and Oxygen

Trifluoromethoxylated aromatics (ArOCF3) are valuable structural motifs in the area of drug discovery due to the enhancement of their desired physicochemical properties upon the introduction of the trifluoromethoxy group (CF3O). Although significant progress has been made recently in the introduction of CF3O group into aromatics, current methods either require the use of expensive trifluoromethoxylation reagents or require harsh reaction conditions. We present a conceptually new and operationally simple protocol for the direct C?H trifluoromethoxylation of (hetero)aromatics by the combination of the readily available trifluoromethylating reagent and oxygen under electrochemical reaction conditions. This reaction proceeds through the initial generation of CF3 radical followed by conversion to CF3O radical, addition to (hetero)aromatics and rearomatization. The utility of this electrochemical trifluoromethoxylation is illustrated by the direct incorporation of CF3O group into a variety of (hetero)aromatics as well as bio-relevant molecules.

Radical C?H Trifluoromethoxylation of (Hetero)arenes with Bis(trifluoromethyl)peroxide

Trifluoromethoxylated (hetero)arenes are of great interest for several disciplines, especially in agro- and medicinal chemistry. Radical C?H trifluoromethoxylation of (hetero)arenes represents an attractive approach to prepare such compounds, but the high cost and low atom economy of existing .OCF3 radical sources make them unsuitable for the large-scale synthesis of trifluoromethoxylated building blocks. Herein, we introduce bis(trifluoromethyl)peroxide (BTMP, CF3OOCF3) as a practical and efficient trifluoromethoxylating reagent that is easily accessible from inexpensive bulk chemicals. Using either visible light photoredox or TEMPO catalysis, trifluoromethoxylated arenes could be prepared in good yields under mild conditions directly from unactivated aromatics. Moreover, TEMPO catalysis allowed for the one-step synthesis of valuable pyridine derivatives, which have been previously prepared via multi-step approaches.

Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow

The first example of photocatalytic trifluoromethoxylation of arenes and heteroarenes under continuous-flow conditions is described. Application of continuous-flow microreactor technology allowed to reduce the residence time up to 16 times in comparison t

Silver-Mediated Trifluoromethoxylation of (Hetero)aryldiazonium Tetrafluoroborates

Here we report a silver-mediated trifluoromethoxylation of (hetero)aryldiazonium tetrafluoroborates by converting an aromatic amino group into an OCF3 group. This method, which can be considered to be a trifluoromethoxylation variation of the classic Sandmeyer-type reaction, uses readily available aryl and heteroaromatic amines as starting materials and AgOCF3 as trifluoromethoxylating reagents. The broad substrate scope and simple, mild reaction condition made this transformation a valuable method in constructing aryl-OCF3 bonds.

Method for trifluoro methoxylation of arylamine

The invention provides a method for synthesizing an aryltrifluoromethoxy compound from an arylamine compound. The method comprises the steps of: performing a diazotization reaction on arylamine, and performing a one-pot reaction between the obtained aryl diazonium salt and trifluoromethoxy silver in an acetonitrile solvent so as to obtain the corresponding aryltrifluoromethoxy product. The obtained product has a high yield, and the process is simple.

Radical Trifluoromethoxylation of Arenes Triggered by a Visible-Light-Mediated N?O Bond Redox Fragmentation

A simple trifluoromethoxylation method enables non-directed functionalization of C?H bonds on a range of substrates, providing access to aryl trifluoromethyl ethers. This light-driven process is distinctly different from conventional procedures and occurs through an OCF3 radical mechanism mediated by a photoredox catalyst, which triggers an N?O bond fragmentation. The pyridinium-based trifluoromethoxylation reagent is bench-stable and provides access to synthetic diversity in lead compounds in an operationally simple manner.

Simple Copper Catalysts for the Aerobic Oxidation of Amines: Selectivity Control by the Counterion

We describe the use of simple copper-salt catalysts in the selective aerobic oxidation of amines to nitriles or imines. These catalysts are marked by their exceptional efficiency, operate at ambient temperature and pressure, and allow the oxidation of amines without expensive ligands or additives. This study highlights the significant role counterions can play in controlling selectivity in catalytic aerobic oxidations.

One-pot synthesis of amidoxime via Pd-catalyzed cyanation and amidoximation

A novel "one-pot" reaction was developed for the synthesis of aryl or heteroaryl-substituted amidoxime compounds containing various functional groups. Fluorescence titration experiments coupled with theoretical analysis revealed that the steric hindrance and electronic effects of substituents influence the binding ability of the amidoxime compounds to uranyl ions. This journal is