Electrochemical Oxidative Addition of Nucleophiles on 2‑Arylindoles: Synthesis of C2-Heteroquaternary Indolin-3-ones

Electrochemical Oxidative Addition of Nucleophiles on 2‑Arylindoles: Synthesis of C2-Heteroquaternary Indolin-3-ones

An electrochemical method has been developed to synthesize 2,2-disubstituted indolin-3-ones under mild conditions. A series of nucleophiles have been added to the 2-arylindole-3-ones, generated in situ under metal-free electrochemical oxidative dearomatization of 2-arylindoles, to afford 2,2-disubst...

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Veröffentlicht in:Journal of organic chemistry 2022-12, Vol.87 (23), p.15771-15782
Hauptverfasser: Nagare, Yadav Kacharu, Shah, Imtiyaz Ahmad, Yadav, Jyothi, Pawar, Amol Prakash, Rangan, Krishnan, Choudhary, Rahul, Iype, Eldhose, Kumar, Indresh
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Sprache:eng
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Zusammenfassung:An electrochemical method has been developed to synthesize 2,2-disubstituted indolin-3-ones under mild conditions. A series of nucleophiles have been added to the 2-arylindole-3-ones, generated in situ under metal-free electrochemical oxidative dearomatization of 2-arylindoles, to afford 2,2-disubstituted 3-carbonyl indoles with heteroquaternary centers in 57–79% yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01734