85677-01-6

Upstream product

• 6996-92-5 benzeneseleninic acid 
• 6872-06-6 2-methyl indoline 
• 17697-12-0 benzeneseleninic anhydride 
• 95-20-5 2-methyl-1H-indole 
• 1132-39-4 diphenylselenide 
• 1666-13-3 diphenyl diselenide 
• 591-50-4 iodobenzene 

Downstream Products

• 95-20-5 2-methyl-1H-indole 
• 1666-13-3 diphenyl diselenide 

Relevant academic research and scientific papers

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.

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.

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

An efficient: T -BuOK promoted C3-chalcogenylation of indoles with dichalcogenides

A versatile and efficient method for the synthesis of 3-chalcogenyl-indoles from indoles and dichalcogenides employing t-BuOK as a promoter at room temperature has been achieved. The present protocol exhibited a broad functional group tolerance. Diverse 3-sulfenyl- and 3-selenyl-indoles were rapidly obtained in good to excellent yields with high regioselectivities. It is noteworthy that this transformation was applicable to N-protected and N-unprotected indoles, allowing N-deprotection and C3-chalcogenylation of indoles in one step.

Rose Bengal catalysed photo-induced selenylation of indoles, imidazoles and arenes: A metal free approach

In this report, the highly efficient Rose Bengal-catalysed C(sp2)-H selenylation of indoles, imidazoles and arenes was achieved using a half molar equiv. of diorganoyl diselenides. This metal-free, photo-induced protocol resulted in selenylated

Convenient synthesis of selenyl-indoles via iodide ion-catalyzed electrochemical C-H selenation

Reported herein is a transition metal- and oxidant-free method for the synthesis of selenyl heteroarenes with diselenides through iodide ion-catalyzed electrolytic selenation. This direct C(sp2)-H selenation strategy, with reduced environmental

Direct, Metal-free C(sp2)?H Chalcogenation of Indoles and Imidazopyridines with Dichalcogenides Catalysed by KIO3

Herein, we report a greener protocol for the synthesis of 3-Se/S-indoles and imidazo[1,2-a]pyridines through direct C(sp2)?H bond chalcogenation of heteroarenes with half molar equivalents of different dichalcogenides, using KIO3 as a non-toxic, easy-to-handle catalyst and a stoichiometric amount of glycerol. The reaction features are high yields, based on atom economy, easy performance on gram-scale, metal- and solvent-free conditions as well as applicability to different types of N-heteroarenes.

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.

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.

Visible-light-mediated aerobic selenation of (hetero)arenes with diselenides

The first visible-light driven aerobic oxidation for the direct selenation of (hetero)arenes has been developed at room temperature, providing an eco-friendly, atom-economical protocol to prepare unsymmetrical selenides from easily accessible diselenides.