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TEMPO-Catalyzed Aerobic Oxidative Selenium Insertion Reaction: Synthesis of 3‑Selenylindole Derivatives by Multicomponent Reaction of Isocyanides, Selenium Powder, Amines, and Indoles under Transition-Metal-Free Conditions
journal contribution
posted on 2018-02-01, 22:32 authored by Huan Liu, Yi Fang, Shun-Yi Wang, Shun-Jun JiA novel and efficient
approach for the selenium functionalization
of indoles was developed with selenium powder as the selenium source,
catalyzed by 2,2,6,6-tetramethylpiperidinooxy (TEMPO) and employing
O2 as the green oxidant. This protocol provides a practical
route for the synthesis of 3-selenylindole derivatives and has the
advantages of readily available starting materials, mild reaction
conditions, and a wide scope of substrates. Electron spin-resonance
(ESR) studies reveal that the approach involves the formation of nitrogen-centered
radicals and selenium radicals via oxidation of in situ generated selenoates.
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Keywords
reaction conditionsSelenium Powdernitrogen-centered radicalsselenium functionalizationelectron spin-resonanceselenium radicalsTransition-Metal-Free Conditionsapproachselenium powderO 23- selenylindole derivativesTEMPO-Catalyzed Aerobic Oxidative Selenium Insertion ReactionESRMulticomponent Reactionselenium source
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