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Anion‐Dependent Imidazolium‐Based Catalysts for Allylation of Aniline with Tunable Regioselectivity
Author(s) -
AlbertSoriano María,
M. Pastor Isidro
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.202000102
Subject(s) - chemistry , regioselectivity , aniline , catalysis , allylic rearrangement , counterion , bromide , iodide , sn2 reaction , chloride , halide , ionic liquid , combinatorial chemistry , organic chemistry , ion
Metal‐free catalysts based on 1,3‐bis(carboxymethyl)imidazolium halides mediate the reaction between allylic alcohols and anilines, providing the corresponding N ‐, 2‐ and 4‐allylaniline isomers selectively. The imidazolium counterion plays a crucial role in the outcome of the reaction. Thus, while the imidazolium chloride selectively provides the N ‐substituted aniline, the bromide and iodide imidazolium salts produce the 2‐ and 4‐allylaniline isomers, respectively, with excellent selectivities. A set of complementary catalysts, which are available by simple modulation, is here presented to conduct a highly regioselective allylation reaction of anilines. Not only the catalysts are synthesized in a straightforward and easily scalable manner, but they can be recycled and used under solvent‐free reaction condition, due to the favorable interactions with the reactants.