10.1021/acs.orglett.7b03783.s001
Huan Liu
Huan
Liu
Yi Fang
Yi
Fang
Shun-Yi Wang
Shun-Yi
Wang
Shun-Jun Ji
Shun-Jun
Ji
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
American Chemical Society
2018
reaction conditions
Selenium Powder
nitrogen-centered radicals
selenium functionalization
electron spin-resonance
selenium radicals
Transition-Metal-Free Conditions
approach
selenium powder
O 2
3- selenylindole derivatives
TEMPO-Catalyzed Aerobic Oxidative Selenium Insertion Reaction
ESR
Multicomponent Reaction
selenium source
2018-02-01 22:32:10
Journal contribution
https://acs.figshare.com/articles/journal_contribution/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/5848011
A 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-tetramethylÂpiperidinooxy (TEMPO) and employing
O<sub>2</sub> 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 <i>in situ</i> generated selenoates.