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Iron‐Based Imidazolium Salts as Versatile Catalysts for the Synthesis of Quinolines and 2‐ and 4‐Allylanilines by Allylic Substitution of Alcohols
Author(s) -
Trillo Paz,
Pastor Isidro M.
Publication year - 2016
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.201600315
Subject(s) - chemistry , aniline , catalysis , quinoline , alkylation , allylic rearrangement , substitution reaction , nucleophilic substitution , organic chemistry , tsuji–trost reaction , combinatorial chemistry , nucleophile , medicinal chemistry
Readily available iron(III)‐based imidazolium salts have proven to be very versatile catalysts for the allylic substitution reaction of alcohols with anilines, allowing the synthesis of quinolines, 2‐allylanilines and 4‐allylanilines just by modulating the reaction conditions. Noteworthy, the formation of quinoline derivatives proceeds by ortho ‐allylation of the corresponding aniline and subsequent oxidative cyclization mediated by atmospheric oxygen. The reaction using anilines as nucleophiles is selective to the C‐alkylation versus the N‐alkylation, under any reaction conditions studied.