Zinc‐Catalyzed N‐Alkylation of Aromatic Amines with Alcohols: A Ligand‐Free Approach
V. Kasi Sankar, Murugavel Kathiresan, Bitragunta Sivakumar, Subramaniyan Mannathan
Abstract
Abstract An efficient zinc‐catalyzed N‐alkylation reaction of aromatic amines was achieved using aliphatic, aromatic, and heteroaromatic alcohols as the alkylating reagent. A variety of aniline derivatives, including heteroaromatic amines, underwent the N‐alkylation reaction and furnished the corresponding monoalkylated products in good to excellent yields. The application of the reaction is also further demonstrated by the synthesis of a 2‐phenylquinoline derivative from acetophenone and 2‐aminobenzyl alcohol. Deuterium labeling experiments show that the reaction proceeds via a borrowing hydrogen process. magnified image
Topics & Concepts
ChemistryAlkylationAnilineReagentCatalysisAlcoholAcetophenoneOrganic chemistryZincLigand (biochemistry)Combinatorial chemistryMedicinal chemistryReceptorBiochemistryAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisCarbon dioxide utilization in catalysis