57204-86-1

Upstream product

• 402-51-7 4-(trifluoromethyl)phenylmagnesium bromide 
• 455-13-0 4-Iodobenzotrifluoride 
• 109541-76-6 tris(4-(trifluoromethyl)phenyl)bismuthane 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 402-43-7 p-trifluoromethylphenyl bromide 

Downstream Products

• 104637-92-5 2-<(4-trifluoromethylphenyl)seleno>-1,3-dithiane 
• 137540-74-0 (Z)-1,2-bis<<(p-trifluoromethyl)phenyl>seleno>-1-octene 
• 137540-80-8 (Z)-1,3-bis<<(p-trifluoromethyl)phenyl>seleno>-2-nonen-1-one 
• 137540-80-8 (E)-1,3-bis<<(p-trifluoromethyl)phenyl>seleno>-2-nonen-1-one 
• 137540-74-0 C₂₂H₂₂F₆Se₂ 
• 71912-37-3 4-(trifluoromethyl)benzeneselenenyl chloride 
• 196092-17-8 (1S,2R,4R)-7,7-Dimethyl-1-(4-trifluoromethyl-phenylselanylmethyl)-bicyclo[2.2.1]heptan-2-ol 
• 1054591-41-1 C₁₅H₉F₃Se 
• 1452862-93-9 4-tolyl 4-(trifluoromethyl)phenyl selenide 

Relevant academic research and scientific papers

Visible Light-Mediated C(sp2)–H Selenylation of Amino Pyrazole and Amino Uracils in the Presence of Rose Bengal as an Organophotocatalyst

Herein, we report an efficient methodology for the synthesis of alkyl, benzyl, and phenyl selenoethers of aminopyrazoles and aminouracils by C(sp2)–H functionalization in the presence of visible light and Rose Bengal as an organophotocatalyst. The reaction of amino pyrazole/iosothiazole/isoxazole or amino uracils with 0.5 equivalent of diphenyl/dibenzyl/diethyl diselenides in the presence of visible light in acetonitrile medium and a catalytic amount of Rose Bengal provided the corresponding phenyl, benzyl, or ethyl selenoethers in good to very good yields. We have also utilized some of the selenylated aminopyrazoles for the preparation of pyrazole-fused dihydropyrimidines tethered with arylselenoethers by a catalyst-free one-pot three-component reaction. The notable features of this methodology are metal-free reaction conditions, good to very good yields, use of an organic photocatalyst, and wide substrate scope; it is also applicable to gram-scale synthesis and provides selenoethers of medicinally important heterocycles such amio-pyrazole, isoxazole, isothiazole, and uracils.

Visible Light-Promoted Selenylation/Cyclization of Enaminones toward the Formation of 3-Selanyl-4H-Chromen-4-Ones

A simple and efficient visible-light-promoted selenylation/cyclization of enaminones have been realized for the practical synthesis of 3-selanyl-4H-chromen-4-ones. This reaction is performed in the mild conditions, no transition metal catalyst or photocatalysts and no additional oxidants are required. In addition, the 3-selanyl-4H-chromen-4-ones could be easily converted to selanyl-functionalized pyrimidines by reacting with benzamidine substrates. (Figure presented.).

Highly selective radical isothiocyano-chalcogenization of alkenes with NH4SCN in water

In the presence of catalytic amounts of molecular iodine and stoichiometric potassium persulfate, a green, highly chemoselective, regioselective and cis-selective radical isothiocyano-chalcogenization of alkenes with NH4SCN in water is disclosed. This three component reaction features high selectivities, an environmentally benign process, mild conditions, high yields, excellent functional-group tolerance, and broad substrate scope. The resulting products can be further transformed into other molecules with structural similarities of these compounds to bioactive analogs.

Metal-free synthesis of unsymmetrical selenides from pyridinium salts and diselenides catalysed by visible light

We report the first metal-free selenolations of pyridinium salts with diselenides to prepare unsymmetrical organoselenides catalysed by visible light. This protocol is an efficient and green method for the preparation of unsymmetrical organoselenides because metal-free conditions and readily accessible diselenides are used.

FeCl3-catalyzed three-component aryl-selenylation of alkenes

FeCl3-catalyzed three-component aryl-selenylation of alkenes with good to excellent yields has been disclosed. This method is characterized by synthesis of complicated products in a single-step reaction, simple operation and readily available commercially reagents. Finally, a reasonable mechanism of FeCl3-catalyzed aryl-selenylation is proposed.

Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor-Acceptor Complex and a Reversible Adsorption to Solid Support Strategy

DNA-encoded library (DEL) technology is a powerful tool in the discovery of bioactive probe molecules and drug leads. Mostly, the success in DEL technology stems from the molecular diversity of the chemical libraries. However, the construction of DELs has been restricted by the idiosyncratic needs and the required low concentration (～1 mM or less) of the library intermediate. Here, we report visible-light-promoted on-DNA radical coupling reactions via an electron donor-acceptor (EDA) complex and a reversible adsorption to solid support (RASS) strategy. This protocol provides a unique solution to the challenges of increasing the reactivity of highly diluted DNA substrates and reducing the residues of heavy metals from photocatalysts. A series of on-DNA indole sulfone and selenide derivatives were obtained with good to quantitative conversions. It is anticipated that these mild-condition on-DNA radical reactions will significantly improve the chemical diversity of DELs and find widespread utility to DEL construction.

Nickel-Catalyzed Intramolecular Decarbonylative Coupling of Aryl Selenol Esters

This report describes a method for Ni-catalyzed intramolecular decarbonylative coupling, which enables the conversion of areneselenol esters to diaryl selenides. The inexpensive and readily available catalyst can be employed under mild reaction conditions for the construction of structurally diverse diaryl selenides, including heterocyclic and natural product derivatives. (Figure presented.).

Clarification on the reactivity of diaryl diselenides toward hexacyclohexyldilead under light

In this study, the reactivity of organochalcogen compounds toward a representative alkyl-lead bond compound under light was investigated in detail. Under light irradiation, the Cy-Pb bond of Cy6 Pb2 (Cy = cyclohexyl) undergoes homolytic cleavage to generate a cyclohexyl radical (Cy?). This radical can be successfully captured by diphenyl diselenide, which exhibits excellent carbon-radical-capturing ability. In the case of (PhS)2 and (PhTe)2, the yields of the corresponding cyclohexyl sulfides and tellurides were lower than that of (PhSe)2. This probably occurred due to the low carbon-radical-capturing ability of (PhS)2 and the high photosensitivity of the cyclohexyl-tellurium bond.

Rhodium-Catalyzed Enantioselective Hydroselenation of Heterobicyclic Alkenes

A highly efficient Rh(I)/(S)-xyl-Binap catalytic system is developed for the asymmetric hydroselenation of various nonpolar olefins with diselenides. Under these mild reaction conditions, a wide range of heterobicyclic alkenes give selenol-incorporated adducts in excellent enantioselectivities (up to 97%) along with high yields (up to 96%) by overcoming self-promoted racemic hydroselenation. The strategy is also applied for kinetic resolution of unsymmetric oxabenzonorbornadiene.

Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides

A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72-94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94-99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts. This journal is