85677-00-5

Upstream product

• 496-15-1 1-indoline 
• 6996-92-5 benzeneseleninic acid 
• 17697-12-0 benzeneseleninic anhydride 
• 143-33-9 sodium cyanide 
• 100561-34-0 1,2,2a,3-Tetrahydrobenzindol-5(4H)-one 
• 2179-79-5 phenyl selenocyanate 
• 120-72-9 indole 
• 59875-97-7 2-allyl-1,3-diphenyl-1,3-propanedione 
• 1666-13-3 diphenyl diselenide 
• 591-50-4 iodobenzene 
• 26340-47-6 3-Iodo-1H-indole 
• 31271-90-6 1-(p-toluenesulfonyl)-1H-indole 
• 576-15-8 N-acetylindole 
• 1496-76-0 N-benzoylindole 

Downstream Products

• 1000682-95-0 1-benzyl-3-(phenylselanyl)-1H-indole 
• 104720-97-0 2,3-bis(phenylselenenyl)indole 
• 104720-95-8 phenyl-indolyl-3 selenoxyde 
• 120-72-9 indole 

Relevant academic research and scientific papers

Time-economical synthesis of selenofunctionalized heterocycles via I2O5-mediated selenylative heterocyclization

A time-economical and robust synthesis of various selenofunctionalized heterocycles was accomplished via I2O5-mediated selenocyclizations of olefins with diselenides. Using this method, 116 selenomethyl-substituted heterocycles were

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.

Preparation of selenofunctionalized heterocycles via iodosobenzene-mediated intramolecular selenocyclizations of olefins with diselenides

An intramolecular selenocyclizations of olefins mediated by a commercially available hypervalent iodine(III) reagent, PhIO, was developed. This method provided access to a wide range of selenenylated heterocycles under ambient conditions. The striking advantages of this protocol over all previous methods include mild reaction conditions, easy operation, good yields, high levels of functional group compatibility, large–scale application and suitability for the late-stage functionalization of complex molecules of biological importance.

Arylseleninic acid as a green, bench-stable selenylating agent: Synthesis of selanylanilines and 3-selanylindoles

Arylseleninic acids were used as an electrophilic selenium source in aromatic substitution reactions, using N,N-substituted anilines and indoles as nucleophiles at 70 °C for 6-15 h. A total of fourteen 4-selanylanilines and five 3-selanylindoles were selectively obtained in good to excellent yields. The starting benzeneseleninic acids are easily prepared from the respective diselenides, are bench stable and easy to handle, affording water as the only waste at the end of the reaction. This journal is

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.

Atom-economical selenation of electron-rich arenes and phosphonates with molecular oxygen at room temperature

Organoselenium and selenophosphorus compounds are ubiquitously found in biologically active compounds, agrochemicals, functionalized materials etc. Although selenium is a micronutrient and an essential trace element, its contamination/consumption in highe

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

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.

Synergistic Cooperative Effect of Sodium borohydride-Iodine Towards Cascade C?N and C?S/Se Bond Formation: One-pot Regioselective Synthesis of 3-Sulfenyl/selenyl Indoles and Mechanistic Insight

In this work, a new strategy to synthesize 3-sulfenyl/selenyl indole is reported wherein LC?MS reveals a novel insight into synergistic cooperative effect of NaBH4-I2 which allows cascade C?N and C?S/C?Se bond formations via reduction-nucleophilic cyclization-chalcogenylation, three steps in one-pot, towards regioselective synthesis of diverse 3-chalcogenyl indoles including 5-bromo-3-[(3,4,5-trimethoxyphenyl)thio]-1H-indole, a known lead anticancer compound, directly from 2-amino-phenacylchlorides and thiophenols or disulfides/diselenides in aqueous dioxane under transition-metal-free condition. (Figure presented.).

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.