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Zinc‐Catalyzed N‐Alkylation of Aromatic Amines with Alcohols: A Ligand‐Free Approach
Author(s) -
Sankar Velayudham,
Kathiresan Murugavel,
Sivakumar Bitragunta,
Mannathan Subramaniyan
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000499
Subject(s) - chemistry , alkylation , aniline , reagent , catalysis , alcohol , acetophenone , organic chemistry , zinc , ligand (biochemistry) , combinatorial chemistry , medicinal chemistry , biochemistry , receptor
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.