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Electronic Tuning of Iron–Oxo‐Mediated CH Activation: Effect of Electron‐Donating Ligand on Selectivity
Author(s) -
Hitomi Yutaka,
Arakawa Kengo,
Kodera Masahito
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201302111
Subject(s) - chemistry , substituent , selectivity , regioselectivity , ligand (biochemistry) , moiety , hydroxylation , quinoline , medicinal chemistry , stereochemistry , catalysis , organic chemistry , enzyme , receptor , biochemistry
We have reported previously that an iron(III) complex supported by an anionic pentadentate monoamido ligand, dpaq H (dpaq H =2‐[bis(pyridin‐2‐ylmethyl)]amino‐ N ‐quinolin‐8‐yl‐acetamido), promotes selective CH hydroxylation with H 2 O 2 with high regioselectivity. Herein, we report on the preparation of Fe III –dpaq derivatives that have a series of substituent groups at the 5‐position of a quinoline moiety in the parent ligand dpaq H (dpaq R , R: OMe, H, Cl, and NO 2 ), and examine them with respect to their catalytic activity in CH hydroxylation with H 2 O 2 . As the substituent group becomes more electron‐withdrawing, both the selectivity and the turnover number increase, but the selectivity of epoxidation shows the opposite trend.