Tunable Electrocatalytic Annulations of o-Arylalkynylanilines: Green and Switchable Syntheses of Skeletally Diverse Indoles

Tunable electrocatalytic annulation reactions of o-arylalkynylanilines have been established, leading to green and divergent syntheses of skeletally diverse indoles by adjusting the electrolytes and the solvents. The presence of ammonium halides as the electrolytes enabled the halogenation of o-aryl...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-11, Vol.86 (22), p.15886-15896
Main Authors: Zhang, Jie, Shi, Shao-Qing, Hao, Wen-Juan, Dong, Guo-Yun, Tu, Shu-Jiang, Jiang, Bo
Format: Article
Language:English
Subjects:
Cyclization
Halogenation
Indoles
Solvents
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Summary:Tunable electrocatalytic annulation reactions of o-arylalkynylanilines have been established, leading to green and divergent syntheses of skeletally diverse indoles by adjusting the electrolytes and the solvents. The presence of ammonium halides as the electrolytes enabled the halogenation of o-arylalkynylanilines to give C3-halogenated indoles whereas naphtho­[1′,2′:4,5]­furo­[3,2-b]­indoles could be obtained by changing the electrolyte from ammonium halides to KI. Interestingly, by combining acetone as the solvent and both NH4I and NH4Cl as the electrolytes, the reaction worked through an intramolecular annulation and [5 + 1] cyclization cascade to form naphtho­[1′,2′:5,6]­[1,3]­oxazino­[3,4-a]­indoles.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02898