ElectrochemicalOne- or Two-Electron Oxidation EnablesChemoselective α-Amino C(sp3)–H Arylationand Cyanation

This is the authors' abstract. We don't add key points for this paper.

A controllable one- vs two-electron electrochemical strategy enables chemoselective α-amino C(sp3)-H arylation (secondary amines) or α-cyanation (tertiary N-aryl-THIQs) using 1,4-dicyanobenzene as a dual-function aryl/cyano source. Simple adjustments of electrolysis parameters divert tertiary amines to two-electron iminium/CN- trapping and secondary amines to one-electron radical/radical-anion cross-coupling. The operationally simple, oxidant-free protocol delivers up to 98% yield, tolerates diverse (hetero)arenes, and is demonstrated on a 2 mmol continuous-flow scale.