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Electrochemical Dearomative 2,3-Difunctionalization of Indoles
Ju Wu1, Yingchao Dou1, Régis Guillot1
1Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO, UMR 8182), Equipe MSMT , Univ. Paris Sud, CNRS, Université Paris-Saclay , 15, rue Georges Clémenceau , 91405 Orsay , Cedex, France.
Abstract:
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 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.
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