Azo Coupling of Indoles Revisited: Synthesis of Biindolyl Photoswitches via the Azo-Coupling/C–H Functionalization Domino Approach

Azo Coupling of Indoles Revisited: Synthesis of Biindolyl Photoswitches via the Azo-Coupling/C–H Functionalization Domino Approach

When azo coupling of aryldiazonium salts with indoles was carried out in aprotic nonpolar solvent on air, a pseudo-three-component reaction has been discovered. Azo coupling is followed by a nucleophilic addition of a second indole unit to the indolium intermediate; aromatization and oxidation are a...

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Veröffentlicht in:Journal of organic chemistry 2023-09, Vol.88 (18), p.12949-12957
Hauptverfasser: Bondarev, Vladimir L., Festa, Alexey A., Storozhenko, Olga A., Golantsov, Nikita E., Pappula, Venkatanarayana, Tskhovrebov, Alexander G., Varlamov, Alexey V., Voskressensky, Leonid G.
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Sprache:eng
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Zusammenfassung:When azo coupling of aryldiazonium salts with indoles was carried out in aprotic nonpolar solvent on air, a pseudo-three-component reaction has been discovered. Azo coupling is followed by a nucleophilic addition of a second indole unit to the indolium intermediate; aromatization and oxidation are achieved under air.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.3c00794