104720-96-9

Upstream product

• 83-34-1 3-Methylindole 
• 71098-88-9 N-phenylselanylphthalimide 
• 1132-39-4 diphenylselenide 
• 1666-13-3 diphenyl diselenide 
• 17697-12-0 benzeneseleninic anhydride 
• 4375-15-9 3-methyl-2,3-dihydro-1H-indole 

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.

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.

Selective synthesis of 3-Selanylindoles from Indoles and Diselenides using IK/mCPBA system

In the presence of a catalytic amount of KI combined with oxidant mCPBA, a convenient catalytic procedure is developed for the preparation of 3-selanylindoles from indoles and diselenides. In this protocol, KI is first oxidized by mCPBA into hypoiodous acid, which reacts with diselenide to cleave Se-Se bond. The in situ generated active electrophilic selenium species then reacts with indole, affording 3-selanylindole via an electrophilic substitution mechanism. This catalytic selenation of indoles has mild reaction conditions and is a simple procedure, which extends the synthetic application of KI in organic synthesis.

Novel Bronsted acid catalyzed three-component alkylations of indoles with N-phenylselenophthalimide and styrenes

(Chemical Equation Presented) Novel and efficient Bronsted acid (p-TsOH) catalyzed inter- and intramolecular Friedel-Crafts alkylations have been developed to synthesize selenated three-component coupling and selenation-cyclization indole derivatives. Chemical removal of the phenylseleno moiety was investigated, and the reaction mechanisms were discussed.

STUDIES ON THE REACTION OF PRIMARY AND SECONDARY AMINES WITH PHENYLSELENINIC ANHYDRIDE AND WITH PHENYLSELENINIC ACID

The dehydrogenation under mild conditions of indolines with phenylseleninic anhydride or acid affords good yields of indoles or of 3-phenylselenenyl indoles.Tetrahydroquinoline and -isoquinoline show comparable behaviour.The dehydrogenation of primary amines gives more complicated mixtures from which nitriles and bis-2-phenylselenenylaldehydes can be isolated.