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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container_end_page 15782
container_issue 23
container_start_page 15771
container_title Journal of organic chemistry
container_volume 87
creator Nagare, Yadav Kacharu
Shah, Imtiyaz Ahmad
Yadav, Jyothi
Pawar, Amol Prakash
Rangan, Krishnan
Choudhary, Rahul
Iype, Eldhose
Kumar, Indresh
description 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.
doi_str_mv 10.1021/acs.joc.2c01734
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title Electrochemical Oxidative Addition of Nucleophiles on 2‑Arylindoles: Synthesis of C2-Heteroquaternary Indolin-3-ones
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