81699-91-4

Upstream product

• 2179-79-5 phenyl selenocyanate 
• 623-47-2 propynoic acid ethyl ester 
• 34837-55-3 Phenylselenyl bromide 
• 1666-13-3 diphenyl diselenide 
• 71098-88-9 N-phenylselanylphthalimide 

Downstream Products

• 1237760-45-0 pentaethyl 6-phenylselanyl-benzene-1,2,3,4,5-pentacarboxylate 

Relevant academic research and scientific papers

Ultrasound-promoted regioselective synthesis of chalcogeno-indolizines by a stepwise 1,3-dipolar cycloaddition

A series of new organochalcogen derivatives of indolizines was synthesized in moderate to excellent yields from pyridinium salts and chalcogeno-alkynes. The reaction can be carried out under thermal conditions or by sonochemical processes in short reaction times. The stepwise cycloaddition reaction forming chalcogeno-indolizines is regioselective and extends to a broad range of functional groups. Furthermore, novel chalcogeno-alkynes are reported and the first derivatives of teluro-indolizine are described. The influence of selenium functionalization on the photophysical properties of indolizines is also described, in which the compounds showed absorption in the UV–Vis region around 360 nm and emission in the blue-to-green region. Relatively low fluorescence quantum yield (?fl) values were calculated, in agreement with the chalcogen effect on other heterocycles.

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.).

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.

A General and highly efficient protocol for the synthesis of chalcogenoacetylenes by copper(I)-terpyridine catalyst

A highly efficient copper-catalyzed Csp-X (X = S, Se, Te) bond-forming reaction of terminal alkynes and diorganyl dichalcogenides has been developed. This transformation was realized through the use of copper(I) iodide as a catalyst, 4′-(4-meth

Short and efficient preparation of alkynyl selenides, sulfides and tellurides from terminal alkynes

Diphenyl diselenide reacts with terminal alkynes at room temperature in DMSO in the presence of catalytic amounts of copper iodide to give good to excellent yields of alkynyl phenyl selenides. The reaction occurs under neutral conditions and the solvent a

77Se NMR. 2. The Basis for Application of JSe-Se and JSe-H in Structure Assignments of Mono-, Di-, and Triseleno-Substituted Alkenes

Series of isomeric mono-, di-, and triseleno-substituted alkenes have been synthesized and subjected to 77Se NMR analysis.In di- and triseleno-substituted alkenes stereochemical assignments were obtained by measurements of 77Se-77Se coupling constants.Val

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.

Cu(I)-CATALYZED REACTION OF TERMINAL ALKYNES WITH PHENYL SELENOCYANATE IN THE PRESENCE OF TRIETHYLAMINE. SYNTHESIS OF ALKYNYL SELENIDES

Treatment of terminal alkynes with phenyl selenocyanate in dichloromethane in the presence of CuX(X=CN or Br) and triethylamine at room temperature gave 1-phenylseleno-1-alkynes in high yields.