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Electrochemical Dearomative 2,3-Difunctionalization of Indoles

preprint
submitted on 28.12.2018 and posted on 28.12.2018 by Ju Wu, Yingchao Dou, Régis Guillot, Cyrille Kouklovsky, Guillaume Vincent
We report the use of electrochemistry to perform a direct oxidative dearomatization of indoles leading to 2,3-dialkoxy or 2,3-diazido indolines under undivided conditions at a constant current. This operationally simple electro-oxidative procedure avoids the use of an external oxidant and displays an excellent functional group compatibility. The formation of the two C-O or C-N bonds is believed to arise from the oxidation of the indoles into radical cation intermediates.

Funding

China Scholarship Council (CSC), PhD fellowship to Ju Wu and Yingchaou Dou

ANR-17-CE07-0050 (“ArDCo”), Agence Nationale de la Recherche

History

Email Address of Submitting Author

guillaume.vincent@u-psud.fr

Institution

ICMMO, Univ. Paris Sud, CNRS, Université Paris Saclay

Country

France

ORCID For Submitting Author

0000-0003-3162-1320

Declaration of Conflict of Interest

No conflict of interest

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in Journal of the American Chemical Society

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