100409-88-9

Upstream product

• 825-76-3 α-cyclopropylstyrene 
• 1666-13-3 diphenyl diselenide 
• 536-74-3 phenylacetylene 
• 1663-39-4 tert-Butyl acrylate 
• 103-64-0 bromostyrene 

Relevant academic research and scientific papers

An efficient synthesis of alkynyl selenides and tellurides from terminal acetylenes and diorganyl diselenides or ditellurides catalyzed by recyclable copper oxide nanopowder

Herein, we report an efficient method for the synthesis of alkynyl selenides and tellurides from terminal alkynes and diorganyl diselenides or ditellurides using CuO nanopowder as a recyclable catalyst. This new methodology furnished the desired products in good to excellent yields. Furthermore, the catalyst was easily recovered and reused for further catalytic reactions without loss of activity.

Nitroselenation of carbon-carbon triple bond by PhSeSePh and NO/O2 or NO2

When alkynes were treated with diphenyl diselenide under an atmosphere of nitric oxide and oxygen, nitroselenation of the carbon-carbon triple bond proceeded with a high regioselectivity to give the corresponding 1-nitro-2-phenylseleno alkenes. Similarly, the nitroselenation of alkynes proceeded by the reaction of the alkynes with nitrogen dioxide. The stirring of the 1,2-bis(phenylseleno) alkenes under an atmosphere of nitric oxide and oxygen also gave the corresponding 1-nitro-2-phenylseleno alkenes.

Highly selective sequential addition and cyclization reactions involving diphenyl diselenide, an alkyne, and alkenes under visible-light irradiation

A four-component radical coupling of diphenyl diselenide, an alkyne, and two olefins to form substituted cyclopentanes in good yields is described (see scheme). This selective sequential addition and cyclization is facilitated by the rate of carbon-radical trapping by diphenyl diselenide, appropriate for this transformation, and the efficiency of the 5-exo cyclization. EWG = electron-withdrawing group.

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.

Nitroselenation of carbon-carbon triple bond by PhSeSePh and NO/O2 or NO2

When alkynes were treated with diphenyl diselenide under an atmosphere of nitric oxide and oxygen, nitroselenation of the carbon-carbon triple bond proceeded with a high regioselectivity to give the corresponding 1-nitro-2-phenylseleno alkenes. Similarly,

Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

Alkynyl selenides were synthesized by a straightforward one-pot and three-step methodology, without the need of diselenides as starting reagents, under an oxygen atmosphere and using PEG 200 as the solvent. This procedure involves the in situ generation of dialkyl diselenides through a K3PO4-assisted reaction of an alkyl selenocyanate obtained by a nucleophilic substitution reaction between KSeCN and alkyl halides. Successive reaction with terminal alkynes in the presence of t-BuOK affords the corresponding alkyl alkynyl selenide in moderate to good yields. Finally, this methodology allowed the synthesis of 2-alkylselanyl-substituted benzofuran and indole derivatives starting from convenient 2-substituted acetylenes.

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.

A simple and stereoselective synthesis of (Z)-1,2-bis-arylselanyl alkenes from alkynes using KF/Al2O3

The title compounds were synthesized by a one-pot reaction of diaryl diselenides with terminal alkynes avoiding the previous preparation of arylselanyl alkynes. The reactions were performed under mild conditions with a range of terminal alkynes using KF/A

Reaction of selenostannanes with 1-alkynes in the presence of SnCl 4

(Organylseleno)triethylstannanes RSeSnEt3 (R = Me, Ph) react with 1-hexyne and phenylacetylene in the presence of SnCl4 to give 1,2-bis(organylseleno)-1-organylethenes.

Synthesis of chalcogenides using indium intermediates in aqueous media

Selenides and vinylic selenides were synthesized from their corresponding organic halides and alkynes in aqueous media using indium metal.