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Citation
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HERO ID
3223954
Reference Type
Journal Article
Title
Substrate-dependent aromatic ring fission of catechol and 2-aminophenol with O2 catalyzed by a nonheme iron complex of a tripodal N4 ligand
Author(s)
Lakshman, TR; Chatterjee, S; Chakraborty, B; Paine, TK
Year
2016
Is Peer Reviewed?
Yes
Journal
Dalton Transactions (Online)
ISSN:
1477-9234
Volume
45
Issue
21
Page Numbers
8835-8844
Language
English
PMID
27148606
DOI
10.1039/c5dt04541j
Abstract
The catalytic reactivity of an iron(ii) complex [(TPA)Fe(II)(CH3CN)2](2+) () (TPA = tris(2-pyridylmethyl)amine) towards oxygenative aromatic C-C bond cleavage of catechol and 2-aminophenol is presented. Complex exhibits catalytic and regioselective C-C bond cleavage of 3,5-di-tert-butylcatechol (H2DBC) to form intradiol products, whereas it catalyzes extradiol-type C-C bond cleavage of 2-amino-4,6-di-tert-butylphenol (H2AP). The catalytic reactions are found to be pH-dependent and the complex exhibits maximum turnovers at pH 5 in acetonitrile-phthalate buffer. An iron(iii)-catecholate complex [(TPA)Fe(III)(DBC)](+) () is formed in the ring cleavage of catechol. In the extradiol-type cleavage of H2AP, an iron(iii)-2-iminobenzosemiquinonate complex [(TPA)Fe(III)(ISQ)](2+) () (ISQ = 4,6-di-tert-butyl-2-iminobenzosemiquinonate radical anion) is observed in the reaction pathway. This work shows the importance of the nature of 'redox non-innocent' substrates in governing the mode of ring fission reactivity.
Tags
IRIS
•
Dibutyl Phthalate (DBP)
Database Searches
Litsearch Jan 2016 - July 2016
Pubmed
Excluded: No Primary Data on Health Effects
Not chemical specific
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