1496-15-7

Usage

Type of compound

Xanthone derivative

Contains

Trifluoromethyl group

Industrial applications

Useful in various applications such as pharmaceuticals, dyes, and agrochemicals

Usage

Often used as a building block in organic synthesis

Structure and properties

Unique structure and properties make it a versatile compound with potential applications in materials science and drug discovery

Importance

An important chemical with a range of uses that continues to be studied for new applications.

InChI:InChI=1/C14H7F3O2/c15-14(16,17)8-5-6-12-10(7-8)13(18)9-3-1-2-4-11(9)19-12/h1-7H

Upstream product

• 108-95-2 phenol 
• 871362-15-1 bis(4-(trifluoromethyl)phenyl)iodonium trifluoromethanesulfonate 
• 119-36-8 methyl salicylate 
• 402-45-9 4-hydroxybenzotrifluoride 
• 552-89-6 2-nitro-benzaldehyde 
• 146137-78-2 2-fluoro-5-trifluoromethylbenzaldehyde 
• 188725-94-2 5-trifluoromethyl-2-(phenoxy)benzaldehyde 
• 454-89-7 3-Trifluoromethylbenzaldehyde 
• 90-47-1 xanth-9-one 
• 77152-08-0 trifluoromethylcopper(I) 

Relevant academic research and scientific papers

One-step synthesis of xanthones catalyzed by a highly efficient copper-based magnetically recoverable nanocatalyst

A versatile and highly efficient strategy to construct a xanthone skeleton via a ligand-free intermolecular catalytic coupling of 2-substituted benzaldehydes and a wide range of phenols has been developed. For this purpose, a novel and magnetically recoverable catalyst consisting of copper nanoparticles on nanosized silica coated maghemite is presented. The reaction proceeds smoothly with easy recovery and reuse of the catalyst. The methodology is compatible with various functional groups and provides an attractive protocol for the generation of a small library of xanthones in very good yield.

Synthesis of xanthones from 4-(2-phenoxyphenyl)-1-tosyl-1H-1,2,3-triazole via rhodium-catalyzed annulation/oxidation

A series of xanthone derivatives were synthesized by rhodium-catalyzed cycloaddition and sequential oxidation. The derivatives synthesized for excellent yields, including electron-withdrawing and electron-donating substituents, demonstrated the wide applicability of the proposed approach. The xanthones synthesized with different substituent electron effects may go through the same intermediate via two cycloadditions. It is highlighted that the protocol was exemplified by its successful integration into a one-pot synthesis directly from 1-ethynyl-2-phenoxybenzene. We believe that the current method may be an attractive option for the synthesis of xanthone and its derivatives.

Formation and Disproportionation of Xanthenols to Xanthenes and Xanthones and Their Use in Synthesis

A facile and versatile strategy employing TiCl4-mediated cyclization followed by a Cannizzaro reaction has been developed for the synthesis of various xanthene derivatives. The reaction proceeded smoothly to afford both xanthenes/xanthones or their sulfur derivatives and tolerated a wide range of electronically diverse substrates. Using this methodology, pranoprofen was synthesized in three steps in 59% overall yield from commercially available starting materials.

Aryl Sulfonium Salts for Site-Selective Late-Stage Trifluoromethylation

Incorporation of the CF3 group into arenes has found increasing importance in drug discovery. Herein, we report the first photoredox-catalyzed cross-coupling of aryl thianthrenium salts with a copper-based trifluoromethyl reagent, which enables a site-selective late-stage trifluoromethylation of arenes. The reaction proceeds with broad functional group tolerance, even for complex small molecules on gram scale. The method was further extended to produce pentafluoroethylated derivatives.

Concise synthesis of xanthones by the tandem etherification—Acylation of diaryliodonium salts with salicylates

An efficient synthetic method for multi-substituted xanthones was developed. The reaction of diaryliodonium salts and salicylates was employed for the preparation of the xanthones. This method proceeded through an intermolecular etherification-acylation t

FeCl3 and ether mediated direct intramolecular acylation of esters and their application in efficient preparation of xanthone and chromone derivatives

The direct intramolecular acylation of esters was developed by using the combined system of FeCl3 with Cl2CHOCH3. This unique cooperative system offered a new and efficient approach to biologically important xanthone and chromone derivatives with regioselectivity. Examples were reported, and control experiments were carried out to examine the effect of the benzyl esters and Cl2CHOCH3.

Rhodium-catalyzed xanthone formation from 2-aryloxybenzaldehydes via cross-dehydrogenative coupling (CDC)

A concise and straightforward strategy to construct a xanthone skeleton via an intramolecular cross-dehydrogenative coupling (CDC) of 2- aryloxybenzaldehydes has been developed. The reaction proceeded smoothly without any need of preactivation of the aldehyde group. It can tolerate various functional groups and provides an applicable protocol to construct a wide range of xanthone derivatives.

An aryl to imidoyl palladium migration process involving intramolecular C-H activation

Biologically interesting fluoren-9-one and xanthen-9-one derivatives have been prepared by a novel aryl to imidoyl palladium migration, followed by intramolecular arylation. The fluoren-9-one synthesis appears to involve both a palladium migration mechanism and a C-H activation process proceeding through an unprecedented organopalladium(IV) hydride intermediate. The results from deuterium labeling experiments are consistent with the proposed dual mechanism.