352-67-0

Usage

InChI:InChI=1/C7H4F4O/c8-5-1-3-6(4-2-5)12-7(9,10)11/h1-4H

Upstream product

• 407-13-6 (4-fluoro-phenyl)-trichloromethyl ether 
• 658-75-3 p-fluorophenyl trifluoroacetate 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 
• 17151-47-2 tributyl(4-fluorophenyl)stannane 
• 1765-93-1 4-fluoroboronic acid 
• 96898-10-1 tris(dimethylamino)sulfonium trifluoromethoxide 
• 1394827-04-3 potassium (4-(trifluoromethoxy)phenyl)trifluoroborate 
• 338792-64-6 α,α-difluoro(4-fluorophenoxy)acetic acid 
• 807368-70-3 ethyl 2-(4-fluorophenoxy)-2,2-difluoroacetate 
• 371-41-5 4-Fluorophenol 
• 462-06-6 fluorobenzene 
• 2070902-77-9 trifluoromethyl 4-fluorobenzene-1-sulfonate 
• 371-40-4 4-fluoroaniline 

Downstream Products

• 287952-66-3 tert-butyl 4-(4-(trifluoromethoxy)phenoxy)piperidin-1-carboxylate 
• 74030-45-8 4-(4-(trifluoromethoxy)phenoxy)phenol 
• 123572-62-3 4-fluoro-2-nitro-1-trifluoromethoxy-benzene 
• 124170-06-5 1-fluoro-2-nitro-4-(trifluoromethoxy)benzene 
• 886497-81-0 2-fluoro-5-(trifluoromethoxy)benzaldehyde 
• 1268051-89-3 (5-fluoro-2-trifluoromethoxyphenyl)carbamic acid ethyl ester 
• 116369-23-4 2-fluoro-5-(trifluoromethoxy)aniline 
• 123572-63-4 5-fluoro-2-trifluoromethoxy-phenylamine 
• 1268051-91-7 (3-fluoro-2-iodo-6-trifluoromethoxyphenyl)carbamic acid ethyl ester 
• 1268051-93-9 (3-fluoro-6-trifluoromethoxy-2-trimethylsilanylethynylphenyl)carbamic acid ethyl ester 
• 1268052-01-2 2,2,2-trifluoro-N-(4-fluoro-3-{1-[4-fluoro-1-(2-methoxyethyl)-7-trifluoromethoxy-1H-indole-3-carbonyl]piperidin-4-yl}benzyl)acetamide 
• 182289-80-1 N-[5-(4-Chloro-1-methyl-5-methylsulfanyl-1H-pyrazol-3-yloxy)-2-trifluoromethoxy-phenyl]-acetamide 

Relevant academic research and scientific papers

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.

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

We report the development of photoredox-catalyzed and copper-promoted trifluoromethoxylation of arenediazonium tetrafluoroborates, with trifluoromethyl arylsulfonate (TFMS) as the trifluoromethoxylation reagent. This new method takes advantage of visible-light photoredox catalysis to generate the aryl radical under mild conditions, combined with copper-promoted selective trifluoromethoxylation. The reaction is scalable, tolerates a wide range of functional groups, and proceeds regioselectively under mild reaction conditions. Furthermore, mechanistic studies suggested that a Cs[Cu(OCF3)2] intermediate might be generated during the reaction.

DIFLUOROMETHOXYLATION AND TRIFLUOROMETHOXYLATION COMPOSITIONS AND METHODS FOR SYNTHESIZING SAME

The present invention provides a compound having the structure (I), a processing of making the compound; and a process of using the compound as a reagent for the difluoromethoxylation and trifluoromethoxylation of arenes or heteroarenes.

Redox-Active Reagents for Photocatalytic Generation of the OCF3 Radical and (Hetero)Aryl C?H Trifluoromethoxylation

The trifluoromethoxy (OCF3) radical is of great importance in organic chemistry. Yet, the catalytic and selective generation of this radical at room temperature and pressure remains a longstanding challenge. Herein, the design and development of a redox-active cationic reagent (1) that enables the formation of the OCF3 radical in a controllable, selective, and catalytic fashion under visible-light photocatalytic conditions is reported. More importantly, the reagent allows catalytic, intermolecular C?H trifluoromethoxylation of a broad array of (hetero)arenes and biorelevant compounds. Experimental and computational studies suggest single electron transfer (SET) from excited photoredox catalysts to 1 resulting in exclusive liberation of the OCF3 radical. Addition of this radical to (hetero)arenes gives trifluoromethoxylated cyclohexadienyl radicals that are oxidized and deprotonated to afford the products of trifluoromethoxylation.

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.

Catalytic C?H Trifluoromethoxylation of Arenes and Heteroarenes

The intermolecular C?H trifluoromethoxylation of arenes remains a long-standing and unsolved problem in organic synthesis. Herein, we report the first catalytic protocol employing a novel trifluoromethoxylating reagent and redox-active catalysts for the direct (hetero)aryl C?H trifluoromethoxylation. Our approach is operationally simple, proceeds at room temperature, uses easy-to-handle reagents, requires only 0.03 mol % of redox-active catalysts, does not need specialized reaction apparatus, and tolerates a wide variety of functional groups and complex structures such as sugars and natural product derivatives. Importantly, both ground-state and photoexcited redox-active catalysts are effective. Detailed computational and experimental studies suggest a unique reaction pathway where photoexcitation of the trifluoromethoxylating reagent releases the OCF3 radical that is trapped by (hetero)arenes. The resulting cyclohexadienyl radicals are oxidized by redox-active catalysts and deprotonated to form the desired products of trifluoromethoxylation.

Fluorodecarboxylation: Synthesis of aryl trifluoromethyl ethers (ArOCF3) and thioethers (ArSCF3)

Fluorodecarboxylation of aryloxydifluoroacetic acid (ArOCF2CO2H) and arylmercaptodifluoroacetic acid (ArSCF2CO2H) towards ArXCF3 (X = O, S) using silver (I) salts in the presence of Selectfluor in a biphasic system with trifluoroacetic acid additive is discussed.

Xenon Difluoride Mediated Fluorodecarboxylations for the Syntheses of Di- and Trifluoromethoxyarenes

XeF2 is demonstrated to be a more proficient fluorine-transfer reagent than either NFSI or Selectfluor in fluorodecarboxylations of both mono- and difluoroaryloxy acetic acid derivatives. This method efficiently converts a wide range of neutral and electron-poor substrates to afford the desired di- and trifluoromethyl aryl ethers in good to excellent yields. The purifications are facile, and the reaction times are less than 5 min, which makes these fluorodecarboxylations promising for future PET-imaging applications.