18782-55-3

Upstream product

• 536-74-3 phenylacetylene 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 95494-85-2 1,2-bis(ethylseleno)-1-phenylethene 
• 89797-54-6 2,5-diiodolselenophene 
• 98-80-6 phenylboronic acid 
• 13466-30-3 (1-phenylethylidene)hydrazine 
• 950894-38-9 2,5-diphenyl-3-iodoselenophene 
• 950894-25-4 (Z)-1-(methylseleno)-1,4-diphenylbut-1-en-3-yne 
• 950894-26-5 (Z)-1-(ethylseleno)-1,4-diphenylbut-1-en-3-yne 
• 950894-29-8 (Z)-1-(tert-butylseleno)-1,4-diphenylbut-1-en-3-yne 
• 950894-31-2 (Z)-1-(benzylseleno)-1,4-diphenylbut-1-en-3-yne 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 685570-02-9 (Z)-1-(n-butylseleno)-1,4-diphenyl-but-1-en-3-yne 
• 495-71-6 phenacylacetophenone 

Downstream Products

• 1354551-09-9 3,4-dibromo-2,5-diphenylselenophene 
• 74084-13-2 5.8-Diphenyl-5.7-dodecadien 

Relevant academic research and scientific papers

An electron spin resonance study of the 2,5-diphenylchalcophene radical ions

The 2,5-diphenylchalcophene radical ions (chalcogen = O, S, Se, Te) have been prepared by the action of alkali metal in 1,2-dimethoxyethane (anions), or by the action of sulphuric acid or thallium(III) trifluoroacetate in trifluoroacetic acid (TFAH) (cati

A novel method for the synthesis of 2,5-diarylselenophenes

The reaction of 4-phenyl- or (2-thienyl)-1,2,3-selenadiazoles with 10 equiv. of arylacetylenes leads to the formation of 2,5-diarylselenophenes in moderate to good yields and 1,4-diarylbuta-1,3-diynes as by-products.

Evidence of a Photoinduced Electron-Transfer Mechanism in the Fluorescence Self-quenching of 2,5-Substituted Selenophenes Prepared through in Situ Reduction of Elemental Selenium in Superbasic Media

A series of new 2,5-disubstituted selenophene derivatives are described from elemental selenium and 1,3-diynes in superbasic media. The activation of elemental selenium in a KOH/DMSO system allows cyclization with conjugated diynes at room temperature. The cyclization reaction is extended to a broad range of functional groups, for which photophysics were experimentally and theoretically investigated. The selenophene derivatives present absorption maxima in the UV-A region and fluorescence emission in the violet-to-blue region. Fluorescence decay profiles were obtained showing a monoexponential decay with fast fluorescence lifetimes (～0.118 ns), as predicted by the Strickler-Berg relations. In general, in both investigations, no dependence on the solvent polarity on the absorption and emission maxima location was observed. On the other hand, solvents and substituents are shown to play a role in the fluorescence quantum yield values. In addition, a fluorescence self-quenching behavior could be observed, related to a photoinduced electron-transfer mechanism. Theoretical calculations performed at the MP2/ADC(2)/cc-pVDZ level of theory were performed in order to investigate the photophysical features of this series of selenophene derivatives.

2,5-disubstituted selenophen compound and synthesis method thereof

The invention belongs to the technical field of organic synthesis, and discloses a 2,5-disubstituted selenophen compound and a synthesis method thereof. The synthesis method comprises the following steps: adding an alkynyl-terminated compound, elemental s

Nickel-catalyzed and Li-mediated regiospecific C-H arylation of benzothiophenes

A nickel-based catalytic system for the regiospecific C2-H arylation of benzothiophene has been established. NiCl2(bpy) is used as a catalyst in combination with LiHMDS as a base in dioxane. The catalytic system is applicable to a variety of functionalized benzothiophenes, as well as other heteroarenes including thiophene, benzodithiophene, benzofuran and selenophene in combination with iodo aryl electrophiles. The role of LiHMDS as a uniquely potent base and a postulated mechanism are discussed. The applicability of this system is finally demonstrated for the synthesis of an intermediate of an active pharmaceutical ingredient.

Transition-Metal-Free Highly Chemoselective and Stereoselective Reduction with Se/DMF/H2O System

A novel metal-free reduction system, in which H2Se (or HSe-) produced in situ from Se/DMF/H2O acts as the active reducing species, has been developed. By using water as an inexpensive, safe, and environmentally friendly surrogate as the hydrogen donor, this new reduction system incorporating Se/DMF/H2O displayed high selectivity and good activity in the reduction of α,β-unsaturated ketones and alkynes. Therefore, this reduction system has great potential to be a general and practical reduction methodology in organic transformation.

Preparation of 1,3-diphenylselenophenotetraazaporphyrinato ruthenium(II) Bis(4-methylpyridine) by the reaction of 3,4-dicyano-2,5-diphenylselenophene and phthalonitrile: Its optical and electrochemical properties

2,5-Diphenylselenophene (2a) was treated with bromine and then copper(I) cyanide to produce 3,4-dicyano-2,5-diphenylselenophene (4). Compound 4 was mixed with phthalonitrile, and the mixture was reacted with ruthenium(III) trichloride and 4-methylpyridine in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in refluxed 2-ethoxyethanol to give 1,3-diphenylselenophenotetraazaporphyrinato ruthenium(II) bis(4-methylpyridine) (6). The structure of 6 was determined by 1H NMR and fast atom bombardment mass spectrometry (FABMS). In the 1H NMR spectrum, the signals of 4-methylpyridine coordinating to the central ruthenium atom were observed at a higher magnetic field than those of free 4-methylpyridine itself but at a lower magnetic field than those of phthaocyaninato ruthenium(II) bis(4-methylpyridine) (7). The 77Se NMR spectrum of 6 showed one singlet peak at δ = 759.5 ppm, which is a lower magnetic field than those of 2a and 4. The Q band absorption of 6 (λmax = 660 nm) lies at a longer wavelength than does that of 7. Oxidation and reduction potentials of 6 were measured with cyclic voltammetry using Ag/AgNO3 as a reference electrode.

Palladium-catalyzed direct arylation of selenophene

An efficient and convenient method was developed for the regioselective formation of 2-aryl- or 2,5-diarylselenophenes via a palladium-catalyzed direct arylation. This protocol is suitable for a wide range of aryl halides containing different functional groups. The 2-arylated substrates can undergo an additional regioselective direct arylation event furnishing symmetrical or unsymmetrical 2,5-diaryl selenophenes in good yield. Competition experiments and the role of the acid additive are in agreement with a concerted metalation deprotonation (CMD) pathway.

Synthesis of novel 2,5-diarylselenophenes from selenation of 1,4-diarylbutane-1,4-diones or methanol/arylacetylenes

Reaction of 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide [PhP(Se)(μ-Se)]2 (Woollins' reagent, WR) with one equivalent of 1,4-diarylbutane-1,4-diones 1a-g in refluxing toluene affords the corresponding 2,5-diarylselenophenes 2a-g in

Electrophilic cyclization of (Z)-selenoenynes: Synthesis and reactivity of 3-iodoselenophenes

(Chemical Equation Presented) We present here our results of the electrophilic cyclization reaction of (Z)-selenoenynes with different electrophiles such as I2, ICl, PhSeBr, and PhSeCl. The cyclization reaction proceeded cleanly under mild reac