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.