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Easy Synthesis of a Self‐Assembled Imine‐Based Iron(II) Complex Endowed with Crown‐Ether Receptors
Author(s) -
Capocasa Giorgio,
Di Berto Mancini Marika,
Frateloreto Federico,
Lanzalunga Osvaldo,
Olivo Giorgio,
Di Stefano Stefano
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000388
Subject(s) - chemistry , imine , crown ether , aldehyde , steric effects , catalysis , ether , hydroxylation , selectivity , polymer chemistry , organic chemistry , medicinal chemistry , combinatorial chemistry , ion , enzyme
Herein we report that an imine‐based iron complex decorated with crown‐ether moieties self‐assembles in CH 3 CN solution from three building blocks (namely Fe(CH 3 CN) 2 (OTf) 2 , 2‐picolylamine and aldehyde 6a ) added in the proper molar ratio (1:2:2, respectively). Aldehyde 6a , endowed with a benzocrown‐ether receptor, can be prepared in two steps from commercial materials with high yields (79 %) and no need of chromatographic separations. The self‐assembled complex is highly stable in CH 3 CN solution. The complex has been tested as catalyst for the oxidation of aromatic compounds endowed with primary ammonium anchoring group with H 2 O 2 . An unexpected yet moderate selectivity for remote meta over ortho hydroxylation was obtained, which is mainly due to the steric hindrance of the catalyst.