Electrochemical Dearomative 2,3-Difunctionalization of Indoles

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.