1000682-94-9

Upstream product

• 603-76-9 1-methylindole 
• 1132-39-4 diphenylselenide 
• 2179-79-5 phenyl selenocyanate 
• 120-72-9 indole 
• 67-56-1 methanol 
• 1666-13-3 diphenyl diselenide 
• 5707-04-0 Phenylselenyl chloride 
• 71098-88-9 N-phenylselanylphthalimide 
• 591-50-4 iodobenzene 

Relevant academic research and scientific papers

Visible-light-induced metal and reagent-free oxidative coupling of: Sp 2 C-H bonds with organo-dichalcogenides: Synthesis of 3-organochalcogenyl indoles

Here, a unique visible-light-induced method for the organochalcogenation of the sp2 C-H bonds of indoles and aniline has been presented using diaryl dichalcogenides (S, Se, and Te) and oxygen as an oxidant avoiding a photocatalyst, base, catalyst, and reagent in acetone at room temperature. This benign protocol allows one to access a wide range of 3-arylselenylindoles, 3-arylthioindoles and even 3-aryltelluroindoles with good to excellent yields. Various functionalities namely, methoxy, and halo either on indoles or aryl dichalcogenides showed amenability to the developed reaction. Furthermore, thiocyanation of the sp2 C-H bonds of indoles has been accomplished by this visible light induced method. A mechanistic understanding by UV-visible, EPR spectroscopy, and cyclic voltammetry suggests that light induces electron transfer from the electron rich arene to oxygen providing an arene radical cation and a superoxide radical anion. Subsequently, reaction of the radical cation with aryl dichalcogenides provides a diaryl chalcogenyl cation which upon removal of protons gave unsymmetrical 3-indolyl aryl chalcogenides.

Direct selenation of imidazoheterocycles and indoles with selenium powder in a copper-catalyzed three-component one-pot system

An efficient and convenient Cu-catalyzed three-component reaction is described for the selenation of imidazoheterocycles/indoles with Se powder and aryl iodides. This procedure provides diverse 3-arylselenylimidazoheterocycles and 3-arylselenylindoles with good yields and functional group tolerance. Some of the products exhibited better or comparable antiproliferative activities compared with the positive control 5-fluorouracil against H1975, PC-9, HGC-27, EC-109, and MCF-7 cancer cell lines.

NaBr mediated regioselective synthesis of 3-Selanylindoles

A convenient NaBr mediated procedure is developed for the preparation of 3-selanylindoles from indoles and diselenides. In this protocol, NaBr is first oxidized by mCPBA into molecular bromine, which reacts with diselenide to form RSeBr. The in situ generated active electrophilic selenium species, then reacts with indoles, affording a series of 3-selanylindoles with high regioselectivity and in moderate to good yields.

Multistep Synthesis of Organic Selenides under Visible Light Irradiation: A Continuous-Flow Approach

The potential application of multistep continuous-flow systems has had a great impact on the syntheses of active pharmaceutical ingredients, natural products, and commodity chemicals. In this report, the highly efficient combination of a chemical reduction and a photochemical Csp2-H activation reaction for selenylation of biologically relevant electron-rich arenes was achieved by means of a continuous-flow process. First, the reduction of alkyl and aryl selenocyanates by Rongalite was achieved giving the corresponding diselenides; second, the photoactivation of the Se-Se bond resulted in the selenylation of electron-rich arenes, both steps from good to excellent yields. In all cases, the reaction time was shortened, and isolated yields were improved when compared to batch reaction conditions. Furthermore, connecting both reactions in a multistep continuous-flow sequence was possible even when reductive and photooxidative transformations were coupled.

Transition-Metal-Free HFIP-Mediated Organo Chalcogenylation of Arenes/Indoles with Thio-/Selenocyanates

We have developed a protocol for the synthesis of diaryl thio-/selenoethers by the reaction of aryl chalcogenocyanates with electron rich arenes/hetero arenes via HFIP promoted C-H activation. The reaction produces chalcogenides in good to excellent yields under mild conditions without the need of a transition metal as a catalyst. The HFIP-mediated reactions tolerated a wide range of functional groups and set the stage for the synthesis of diversely decorated chalcogenides. A mechanism involving activation of the C-H bond through hydrogen bonding is proposed.

Automated Electrochemical Selenenylations

Integrated electrochemical reactors in automated flow systems were utilised for selenenylation reactions. The automation allowed multiple electrochemical reactions of a programmed sequence to be performed in a fully autonomous way. Many functionalised selenenylated products were synthesised in short reaction times in good to high yields.

Conjugated microporous polymer based on phenothiazine, preparation method and efficient catalytic application

The invention discloses a conjugated microporous polymer based on phenothiazine, a preparation method and an efficient catalytic application and belongs to the technical field of photocatalytic functional material preparation. The conjugated microporous polymer based on carbazole-phenothiazine has a high specific surface area, excellent heat stability and chemical stability and good ultraviolet absorption, has good photocatalytic activity, and can catalyze aerobic selenylation of indole efficiently in an illuminating aerobic condition. The conversion ratio is greater than 99%. As a heterogeneous catalyst, the polymer is separated and recovered conveniently and can be recycled. The conjugated microporous polymer based on phenothiazine expands the application of CMPs in photocatalysis and has important application value and application prospect.

Fe(III)-Catalyzed direct C3 chalcogenylation of indole: The effect of iodide ions

A mild and efficient iron (III)-catalyzed C3 chalcogenylation of indoles has been developed and the role of the iodide ions in this transformation was investigated. EPR experiments revealed the reduction of Fe(III) to Fe(II) under the reaction conditions, supporting the formation of molecular iodine in the system, which in effect catalyze the reaction. The scope of the chalcogenylation was broad and the synthesis of more functionalized 3-selenylindoles was explored.

Metal- and photocatalyst-free synthesis of 3-selenylindoles and asymmetric diarylselenides promoted by visible light

A novel and sustainable procedure was developed for the synthesis of 3-selenylindoles employing diorganyl diselenides and indoles or electron-rich arenes as starting materials. Visible blue light was used to promote the reaction without employing transiti

Preparation method of 3-arylseleno-1H-indoles

The invention provides a preparation method of 3-arylseleno-1H-indoles. Specifically, corresponding 3-arylseleno-1H-indoles are generated from aromatic heterocyclic compounds and symmetric diselenidesthrough a reaction in an organic solvent under irradiation of a blue LED lamp, preferably, the reaction is performed in presence of FIrPic (bis(4,6-difluorophenylpyridinato-N,C2)picolinatoiridium). The preparation method is simple and convenient to operate, a reagent is obtained easily, a catalyst is safe and pollution-free, the requirement of green chemistry is met, and the catalyst is stable inproperty and high in catalytic efficiency; yield and purity of 3-arylseleno-1H-indoles prepared with the method are both higher.