30665-96-4

Upstream product

• 34837-55-3 Phenylselenyl bromide 
• 4440-01-1 lithium phenylacetylide 
• 1666-13-3 diphenyl diselenide 
• 85143-25-5 C₁₅H₁₅N₃OSe 
• 918487-96-4 2-phenyl-1-ethynylboronic acid 
• 159087-45-3 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane 
• 103-64-0 bromostyrene 
• 536-74-3 phenylacetylene 
• 74-88-4 methyl iodide 
• 637-44-5 phenylpropyolic acid 
• 81926-79-6 benzeneselenenyl iodide 
• 591-50-4 iodobenzene 
• 2179-79-5 phenyl selenocyanate 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 28622-61-9 butyl phenyl selenide 
• 637-44-5 phenylpropyolic acid 
• 7392-13-4 (Z)-α,β-bis(phenylseleno)styrene 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 60466-40-2 (E)-phenyl(styryl)selane 
• 536-74-3 phenylacetylene 
• 1817-57-8 4-phenyl-3-butyne-2-one 
• 673-32-5 1-Phenylprop-1-yne 
• 60466-30-0 (Z)-β-(phenylseleno)styrene 
• 165278-87-5 (E)-1-bromo-1-(phenylselanyl)-2-phenylethene 
• 30876-65-4 2-phenyl-1-(phenylseleno)ethanone 
• 1035645-38-5 C₁₈H₂₀SeTe 

Relevant academic research and scientific papers

THE REACTION OF TERMINAL ALKYNES WITH THE REAGENT PREPARED FROM BENZENESELENENYL BROMIDE AND SILVER NITRITE. NOVEL EFFICIENT SYNTHESIS OF 1-ALKYNYL PHENYL SELENIDES

1-Alkynyl phenyl selenides were synthesized in good yields by the reaction of 1-alkynes with a new reagent prepared from benzeneselenenyl bromide and silver nitrite.

Organo-selenium mediated regio- and stereoselective iodoselenylation of alkynes in an aqueous medium: Simple access to (: E)-β-iodoalkenyl selenides

A method for the simple and efficient iodoselenylation of simple alkynes under mild conditions using commercially available molecular iodine (I2) and diorganoyldiselenides as starting materials has been developed. A broad range of alkynes can b

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.

Rhodium(I)-Catalyzed Regioselective Azide-internal Alkynyl Trifluoromethyl Sulfide Cycloaddition and Azide-internal Thioalkyne Cycloaddition under Mild Conditions

A regioselective method to access fully substituted 5-trifluoromethylthio-1,2,3-triazoles and 5-thio-1,2,3-triazoles from the internal alkynyl trifluoromethyl sulfides and internal thioalkynes by a rhodium(I)-catalyzed azide-alkyne cycloaddition (RhAAC) reaction under mild conditions has been developed. This approach features good compatibility with water and air, a broad substrate scope, good functional group tolerance, high yields and excellent regioselectivities. The high 1,5-regioselectivities were controlled by the strong coordination between the sulfur atom and the π-acidic rhodium. The advantages of this method further include its applicability to gram-scale preparation, the use of solid-phase synthesis technique, and the mutually orthogonal CuAAC-RhAAC reaction. (Figure presented.).

Accessing the Rare Diazacyclobutene Motif

A formal [2 + 2] cycloaddition of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) with electron-rich alkynyl sulfides and selenides is described. These investigations provide a convenient method to access diazacyclobutenes in good yield while tolerating a rela

Copper-Catalyzed Decarboxylative/Click Cascade Reaction: Regioselective Assembly of 5-Selenotriazole Anticancer Agents

A simple and efficient Cu-catalyzed decarboxylative/click reaction for the preparation of 1,4-disubstituted 5-arylselanyl-1,2,3-triazoles from propiolic acids, diselenides, and azides has been developed. The mechanistic study revealed that the intermolecular AAC reaction of an alkynyl selenium intermediate occurred. The resulting multisubstituted 5-seleno-1,2,3-triazoles were tested for in vitro anticancer activity by MTT assay, and compounds 4f, 4h, and 4p showed potent cancer cell-growth inhibition activities.

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.

Copper-Silver Dual Catalyzed Decyanative C–Se Cross-Coupling

Traditionally, a metal-catalyzed cross-coupling reaction is governed by displacement of leaving groups such as halogens, tosylates, etc. by different nucleophiles leading to the formation of carbon-carbon and carbon-heteroatom bonds. Besides displacement of traditional leaving groups in coupling reactions decyanative cross-coupling has also received current attention. The objective of this work is to develop a decyanative cross-coupling through metal-assisted nucleophilic displacement, which is less explored so far. Thus, a decyanative cross-coupling of aryl selenocyanate with aryl-/alkylacetylenes, boronic acids and silanes has been accomplished by a copper-assisted nucleophilic displacement reaction for an easy access to a series of diaryl, aryl alkyl, aryl vinyl and aryl alkynyl selenides. The best yield of product was obtained using 5 mol% of Cu(OAc)2, Ag2CO3(20 mol%) and Cs2CO3(1 equiv.) at 100 °C for 8 h in N-methylpyrrolidinone (NMP). The advantages of simple operation, high yields and general applicability make this procedure more attractive. A mechanistic pathway has been proposed. Silver plays a key role in the decyanation process. A plausible mechanistic pathway of this decyanative carbon-selenium cross-coupling has been proposed based on UV, EPR, HR-MS and IR analytical data along with results obtained from control experiments. (Figure presented.).

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.

Copper nanoparticles catalyzed Se(Te)-Se(Te) bond activation: A straightforward route towards unsymmetrical organochalcogenides from boronic acids

A highly porous copper metal-organic framework, [Cu3(BTC)2] (BTC=benzene-1,3,5-tricarboxylate) was synthesized and used as a precursor for the synthesis of copper nanoparticles (NPs) and characterized by several techniques, including XRD, SEM, TEM, EDX and BET measurements. The as-synthesized copper nanoparticles were immobilized onto activated charcoal (AC) by means of ultrasonication at room temperature without any pretreatment. The Cu NPs/AC was employed as a heterogeneous catalyst for the cross-coupling of diphenyl diselenide and boronic acids to form diphenyl selenides through Se-Se bond activation under ligand-, base-, and additive-free conditions. The copper NPs/AC, which combines the architecture of MOFs and the high surface area of charcoal, could be an efficient heterogeneous catalytic system that is compatible with a variety of substituents on diphenyl selenides. Its promising catalytic activity relative to that of other homogeneous systems and low catalyst loading for the synthesis of unsymmetrical diaryl selenides is an important application in the area of nanocatalysis. The Cu NPs/AC catalyst, which exhibits excellent catalytic activity and remarkable tolerance to a wide variety of substituents, led to Se sp3-, sp2-, and sp-carbon bond formation by using DMSO as a solvent and atmospheric air as oxidant. This approach can also be extended to the preparation of unsymmetrical organotelluride derivatives. Three-in-one catalyst: Copper nanoparticles on activated charcoal show excellent catalytic activity towards the synthesis of unsymmetrical chalcogenides, starting from boronic acids, in air under ligand-, base-, and additive-free conditions, and resulting in selenium sp3-, sp2-, and sp-carbon bond formation.