A paired electrolysis enabled cascade annulation that enables the efficient synthesis of highly functionalized quinoline-substituted bioactive molecules from readily available starting materials is reported.

Scheme 1. Electrochemical N-nitrosation using sodium/potassium nitrite as nitrosating agents.

The site‐selective functionalization of biologically important nitrogen‐containing heterocycles and related derivatives remains a challenging and important task. We report herein on the direct regiodivergent N1/C2 phosphorylation of free indole derivatives. Cyclic voltammograms and EPR data indicate that by utilizing different electrolyte‐mediated anodic oxidation to generate different active indole species, a diverse collection of N1 and C2 phosphorylation products could be obtained in moderate to high yields under exogenous‐oxidant‐free and metal‐catalyst‐free electrochemical conditions. In addition, N−P coupling was also found to be compatible with various alkylamines.

Herein, we report an electrochemically promoted chemoselective hydroxyl group transformation for accessing of tyrosine-contained biomolecules with valuable anthranilic acid derivatives. Notably, this method utilizes fluoride anion as electrolyte and hydrogen-bonding...