91585-32-9

Upstream product

• 107378-45-0 1-(4-Methoxy-phenylethynylselanyl)-propan-2-one 
• 107378-44-9 2-(4-Methoxy-phenylethynylselanyl)-1-phenyl-ethanone 
• 1777-55-5 (4-methoxyphenacylidene)triphenyl phosphorane 
• 71098-88-9 N-phenylselanylphthalimide 
• 768-60-5 4-methoxyphenylacetylen 
• 1666-13-3 diphenyl diselenide 
• 33675-41-1 1-bromo-2-(4-methoxyphenyl)acetylene 
• 34837-55-3 Phenylselenyl bromide 
• 57444-37-8 Potassium; (4-methoxy-phenyl)-ethyneselenolate 
• 27892-76-8 4-(4-methoxy-phenyl)-[1,2,3]selenadiazole 
• 91585-39-6 1-(4-methoxyphenyl)-2-(phenylselanyl)-2-(triphenylphosphaneylidene)ethan-1-one 

Downstream Products

• 28622-61-9 butyl phenyl selenide 
• 2227-57-8 3-(4-methoxyphenyl)propynoic acid 

Relevant academic research and scientific papers

A Unified Approach for Divergent Synthesis of Heterocycles via TMSOTf-Catalyzed Formal [3+2] Cycloaddition of Electron-Rich Alkynes

We present a synthetic protocol for the construction of polysubstituted five-membered heterocycles via TMSOTf-catalyzed formal [3+2] cycloaddition of electron-rich alkynes, which features free from any metal, atom economy and water as the main by-product. Furthermore, alkenyl ether adduct has been verified as the key intermediate. Notably, by utilizing this approach, we can synthesize a broad range of polysubstituted furans, thiophenes and pyrroles, and extend this transformation to deliver fused-polyheterocycles. This reaction can be achieved on a gram scale and the corresponding products are intermediates for producing diverse potentially useful scaffolds. (Figure presented.).

New arylselanylpyrazole-copper catalysts: Highly efficient catalytic system for C–Se and C–S coupling reactions

We describe herein the use of arylselanylpyrazole–copper complexes as versatile catalysts for C–Se and C–S coupling reactions. The performance of these complexes for C–Se reactions was investigated in chalcogenoacetylene synthesis. The reactions were carried out under mild and aerobic conditions and afforded selanylalkynes bearing a variety of electron-withdrawing and electron-donating groups. The performance of these catalysts for C–S coupling was investigated through the reaction of aryl halides with thiols and products were obtained in moderate to excellent yields. A plausible mechanism for selenoacetylene synthesis is also suggested, and the 77Se NMR results show that these arylselanylpyrazole ligands act as hemilabile ligands. High-resolution mass spectrometry was used to investigate the intermediates and also to corroborate the proposed catalytic cycle.

Silver-catalyzed carbon-selenium cross-coupling using N-(phenylseleno)phthalimide: An alternate approach to the synthesis of organoselenides

Silver(I) catalyzed phenylselenylation of terminal alkynes and organoboronic acids has been demonstrated using N-(phenylseleno)phthalimide as an electrophilic SePh donor. A wide variety of terminal alkynes and organoboronic acids are selenylated efficiently to produce the corresponding alkynyl and diaryl selenides, respectively, in good yields. Silver(I) acts as a Lewis acid in this process.

Mechanochemical Synthesis of Active Magnetite Nanoparticles Supported on Charcoal for Facile Synthesis of Alkynyl Selenides by C?H Activation

Magnetite (Fe3O4) nanoparticles supported on charcoal, graphene, or SBA-15 were prepared by a simple solid-state grinding technique and subsequent thermal treatment. The Fe3O4 nanoparticles supported on activated charcoal exhibited high catalytic activity and furnished good yields of the alkynyl selenide product in the cross-coupling reaction of diphenyl diselenide and alkynes through activation of C?H and Se?Se bonds under ecofriendly conditions, surpassing traditional copper-based catalysts to effect the same organic transformation.

Magnetite (Fe3O4) nanoparticles: An efficient and recoverable catalyst for the synthesis of alkynyl chalcogenides (selenides and tellurides) from terminal acetylenes and diorganyl dichalcogenides

We present herein a new and efficient methodology for the synthesis of alkynyl chalcogenides from terminal acetylenes and diorganyl dichalcogenides, catalyzed by Fe3O4 nanoparticles. This new approach provided the desired products in good to excellent yields. Moreover, the catalyst was easily recoverable using an external magnet and reused for further experiments without loss of catalytic activity.

An efficient and general procedure for the synthesis of alkynyl chalcogenides (selenides and tellurides) by alumina-supported Cu(II)-catalyzed reaction of alkynyl bromides and diphenyl dichalcogenides

Alumina (Al2O3) supported Cu(II) efficiently catalyzes the reaction of alkynyl bromides and diphenyl diselenides and ditellurides in presence of Zn dust or indium(I) bromide to provide the corresponding alkynyl selenides and tellurides. The reactions of a wide variety of substituted alkynyl bromides have been addressed. The zinc dust or InBr is required for the cleavage of diphenyl selenides/tellurides. The mechanism of the reaction is established. The yields of products are high and the catalyst is recycled.

An efficient and general procedure for the synthesis of alkynyl chalcogenides (selenides and tellurides) by alumina-supported Cu(II)-catalyzed reaction of alkynyl bromides and diphenyl dichalcogenides

Alumina (Al2O3) supported Cu(II) efficiently catalyzes the reaction of alkynyl bromides and diphenyl diselenides and ditellurides in presence of Zn dust or indium(I) bromide to provide the corresponding alkynyl selenides and tellurides. The reactions of a wide variety of substituted alkynyl bromides have been addressed. The zinc dust or InBr is required for the cleavage of diphenyl selenides/tellurides. The mechanism of the reaction is established. The yields of products are high and the catalyst is recycled.

Syntheses of β-Hydroxyselenides and Selenides from 1,2,3-Selenadiazoles: Selenophilic Reaction of Phenylmagnesium bromide on α-Selenoketones

α-Selenoketones were prepared starting from 1,2,3-selenadiazoles and α-haloketones and were reduced to corresponding β-hydroxyselenides.The action of phenylmagnesium bromide on α-selenoketones was studied.Selenium was the site of nucleophilic attack by Grignard reagent.