Diazonium Salts as Nitrogen-Based Lewis Acids

Abstract

Aryldiazonium salts are widely used in many organic transformations with displacement of N2 or through addition to the terminal nitrogen. Such aryldiazonium salts can be viewed as N-based Lewis acids that can react with Lewis bases to synthesize a wide variety of azo compounds. Additionally, diazonium salts are known to undergo single-electron transfer and release N2, forming an aryl radical, which results in different reactivity. Herein, we provide a concise overview of the reactivity of aryldiazonium salts undergoing classical donor-acceptor reactivity or single-electron transfer.