Silver-catalyzed direct selanylation of indoles: synthesis and mechanistic insights

Abstract

We developed a combined experimental and theoretical study that gives mechanistic insights into the silver-catalyzed direct selanylation of indoles.

Selective Synthesis of 3‐Chalcogenylindoles via Silver‐Catalyzed Direct Chalcogenation of Indoles with Dichalcogenides

“…Based on our control experiments and previous reports of silver-catalyzed reactions, [29][30] Additionally, 77 Se NMR spectroscopy measurements were conducted to prove the formation of the silver-diphenyldiselenide intermediate and product 4 a. Product 4 a was analyzed by 77 Se NMR and 1 H NMR.…”

“…The use of silver catalysts in the direct C(sp 2 )À H chalcogenation of indole with di-organyl chalcogenides have been reported however the reactions was achieved using high temperature and long reaction time. [29][30] On the basis of the silver catalyzed cross-coupling reaction of aryl boronic acids with diaryl diselenides [31] and silver-mediated oxidative functionalization of alkylsilanes [32] that simplify the syntheses, both in terms of reducing the number of steps and waste generation. These advantages of the silver catalyst, suggest the possibility for developing new methods for the direct CÀ H chalcogenylation of indoles using AgNO 3 promoted regioselective chalcogenylation of indole derivatives at the C3-position with dichalcogenide (diselenide and disulfide) under aerobic conditions using mild reaction conditions in a short reaction time.…”

Selenium Modification of Natural Products and Its Research Progress

“…The C-H bond is the most common structural fragment in organic compounds. Converting inert C-H bonds into C-Se bonds avoids pre-functionalization steps, thus simplifying the synthesis steps and reducing the generation of by-products, which can achieve a higher atomic economy [70]. Therefore, how to efficiently form selective C-Se bonds is crucial for the synthesis of cyclic selenides.…”

Synthesis of Selenium-Decorated N-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

“…A significant part of the synthetic bioactive organoselenium derivatives are obtained when hybridized with N -based heterocycles, as, for example, in the case of some selenium-decorated quinoline derivatives, which have demonstrated superior anti-inflammatory activity in comparison to Meloxicam . In this context, the main effective synthetic strategies to install organoselenium groups are through the use of Se-based electrophilic reagents (e.g., PhSeCl and PhSeBr) and by the generation in situ of related species in the presence of TM-based catalyst (e.g., Cu, Fe, and Ag) or oxidant species (e.g., I 2 , Oxone, and persulfates) …”