32111-94-7

Upstream product

• 3425-46-5 potassium selenocyanate 
• 104-94-9 4-methoxy-aniline 
• 17333-79-8 p-methoxybenzenediazonium 
• 141339-54-0 bis(4-anisyl)iodonium triflate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 2179-96-6 triselenium dicyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 109-77-3 malononitrile 

Downstream Products

• 109966-47-4 3-methylphenyl 4'-methoxyphenyl selenide 
• 37773-20-9 4-methoxybenzeneselenol 
• 124111-68-8 dichloro-(4-methoxy-phenyl)-p-tolyl-λ⁴-selane 
• 125689-09-0 dichloro-(4-methoxy-phenyl)-m-tolyl-λ⁴-selane 
• 125929-18-2 biphenyl-4-yl-dichloro-(4-methoxy-phenyl)-λ⁴-selane 
• 21506-10-5 1-methoxy-4-[(trifluoromethyl)selanyl]benzene 
• 90158-88-6 4-methylphenyl 4’-methoxyphenyl selenide 
• 94583-63-8 (4-methoxyphenyl)(4-nitrophenyl)selane 
• 38762-70-8 bis(4-methoxyphenyl)diselenide 
• 80448-01-7 p-methoxyphenyl phenyl selenide 
• 17893-48-0 (4-methoxy-phenylselanyl)-acetic acid 
• 109589-02-8 [1,1'-biphenyl]-4-yl(4-methoxyphenyl)selane 

Relevant academic research and scientific papers

Using fluoroform for constructing aromatic and heterocyclic trifluoromethylselenyl compounds

Fluoroform is used to prepare CuCF3 according to literature procedures. This nucleophilic trifluoromethyl moiety was reacted with aromatic and heterocyclic selenium cyanide derivatives to form the corresponding trifluoromethylselenium compounds. Selenium cyanides were made with 1,3-dicyanotriselenide prepared in situ from malononitrile and selenium dioxide. The electrophilicity of the reagent (δ+SeCN) was enough to attack aniline derivatives at the para position, but with other aromatics it was advantageous to use the corresponding boronic acid as the moiety was easily displaced by the selenium cyanate moiety.

Metal-Free Synthesis of Aryl Selenocyanates and Selenaheterocycles with Elemental Selenium

This work reports a green method for the synthesis of aryl selenocyanates via a three-component reaction of arylboronic acids, Se powder, and trimethylsilyl cyanide (TMSCN) under metal-free and additive-free conditions. Remarkably, TMSCN acts as not only the substrate, but also the catalyst. Various selenaheterocycles can be also accessed with a catalytic amount of TMSCN.

An electrochemical method for deborylative seleno/thiocyanation of arylboronic acids under catalyst- And oxidant-free conditions

An electrochemical deborylative seleno/thiocyanation of arylboronic acids has been well established to synthesize the corresponding aryl seleno/thiocyanates with good functional group tolerance under ambient conditions. A gram-scale reaction has been performed to highlight the advantages of the protocol. Preliminary mechanistic studies indicate that the oxidation of the seleno/thiocyanate anion occurs prior to that of the arylboronic acid substrate in galvanostatic mode, and that free radicals are involved in the process.

Synthesis method of aryl selenocyanate compounds

The invention relates to the field of synthesis of chemical products, in particular to a synthesis method of aryl selenocyanate compounds. The method starts from arylboronic acid which is easy to obtain, KSeCN which is the cheapest is used as a selenocyanate source, environment-friendly pollution-free current is adopted as a reaction driver, and under conditions of air and a room temperature, arylselenocyanates are efficiently synthesized. Compared with a conventional aryl selenocyanate synthesis method, the method has the obvious advantages that reaction raw materials (including the arylboronic acid) are cheap and easy to obtain, the current causes the lowest pollution to the environment, multiple kinds of functional groups of aromatic rings have good tolerance, yields are high, and thelike. The method can be applied to synthesis of a wide variety of fields of medicines, materials, natural products and the like of the industrial circles and the academic circles.

Metal-Free ipso -Selenocyanation of Arylboronic Acids Using Malononitrile and Selenium Dioxide

The first ipso -selenocyanation of arylboronic acids is achieved using selenium dioxide and malononitrile under mild conditions. The reaction is successful even without metal or base in DMSO. The major advantages of this new method are an easy set-up, excellent yields, and the use of odorless and inexpensive selenium reagents. Basic conditions subsequently afford new access to diaryldiselenides in good yields without isolating the organoselenocyanate intermediates.

A convenient, transition metal-free synthesis of difluoromethyl selenoethers from organic selenocyanates and TMSCF2H

An efficient and transition metal-free method for the synthesis of aryl or alkyl difluoromethyl selenides (RSeCF2H) from the corresponding selenocyanates (RSeCN) and TMSCF2H/t-BuOK is described. The reaction performed in THF at 0 °C for 24 h or at room temperature for 6 h supplied a series of RSeCF2H in good to high yields. The successful preparation of difluoromethylselenolated sulfadimethoxine derivative and the scaled-up synthesis of 1-benzyl-5-((difluoromethyl)selanyl)indoline, as examples, suggested good practicability of this method. Advantages of the reaction include mild reaction conditions, good functional group tolerance, a wide range of substrates, and high efficiency. This protocol offered a number of novel difluoromethyl selenoethers, which would accelerate use of such compounds in the areas of life science.

Metal-free synthesis of unsymmetrical organoselenides and selenoglycosides

A one-pot, metal-free procedure has been developed to synthesize unsymmetrical organoselenides. In the first step of the reaction, arylation of potassium selenocyanate (KSeCN) with an iodonium reagent proceeds in the absence of a metal catalyst to produce

Trifluoromethylselenolation of Aryldiazonium Salts: A Mild and Convenient Copper-Catalyzed Procedure for the Introduction of the SeCF3 Group

The straightforward introduction of the trifluoromethylseleno group into aromatic and heteroaromatic compounds is accomplished by the utilization of readily available aryldiazonium tetrafluoroborates, potassium selenocyanate, and Ruppert-Prakash reagent. The reaction tolerates a wide range of aromatic and heteroaromatic diazonium salts and is also amenable to the synthesis of pentafluoroethyl selenoethers. Furthermore, the methodology can be applied directly starting from anilines.

Synthesis of novel 5-aryl-1H-tetrazoles

In this study phenylselenocyanate and some of its derivatives (o-Cl, p-Cl, p-Br, o-NO2, p-NO2, o-CH3, p-CH3, o-COOH, p-COOH, p-OCH3 substituted) were synthesized (3a-3j). The synthesized compounds were converted to 5-aryl-1H-tetrazole (4a-4j), by Et 3N · HCl-NaN3 in toluene, which are a new series of phenylselanyl-1H-tetrazoles. The structure of all the presently synthesized compounds were confirmed using spectroscopic methods (FTIR, 1H NMR, MS).

Reaction of Areneselenyl Chlorides and alkenes. An example of Nucleophilic Displacement at Bivalent Selenium

The effect of substituents in the phenyl ring of both the electrophile and the alkene has been studied in the reaction of areneselenyl chlorides and (E)- and (Z)-1-phenylpropenes.Electron-donating groups in both phenyl rings enhance the rate of reaction.Viewing this reaction as a nucleophilic displacement at bivalent selenium leads to a model that allows the possibility of reaction by a continuum of mechanisms.These mechanisms differ only in the relative amounts of C-Se bond making and Se-Cl bond breaking in the rate-determining transition state.From our data, it is concluded that C-Se bond making lags behind Se-Cl bond breaking in the rate determining transition state.