tBu₄NCl/K₂S₂O₈ System Induced C‐2 Functionalization of 8‐Aminoquinoline Amides with Primary Alcohols

Abstract

A metal and light‐free Minisci‐type acylation approach of 8‐aminoquinoline amides with general primary alcohols was demonstrated under tBu4NCl/K2S2O8 system. Simultaneously, the C2−H alkylation can be realized by accident for special benzyl alcohols bearing strong electron‐donating groups. Most N‐heterocycles were also compatible to afford corresponding acylated products. Furthermore, the mechanism investigation reveals that chlorine radical induced the original ketyl radical generation through abstracting the α‐C−H from the alcohols, then underwent nucleophilic carbon‐centered radicals addition, deprotonation, and oxidation to provide the target acylation products.