Preparation of 4,7-diphenyl-1,10-phenanthroline-2,9-dicarboxylic acid catalyzed by iron(III)porphyrins with (diacetoxyiodo)benzene.

Abstract:

:Using iron(III)porphyrins in combination with (diacetoxyiodo)benzene allows for the conversion of 2,9-bis(bromomethyl)-4,7-diphenyl-1,10-phenanthroline into 4,7-diphenyl-1,10-phenanthroline-2,9-dicarboxylic acid. This method provides a cost-effective and environmentally-friendly oxidation procedure using less toxic PhI(OAc)2 and biologically relevant iron(III)porphyrins. The catalytic activity of five kinds of iron-metallated functional porphyrins were investigated using different oxidants, including air, H2O2, PhI(OAc)2, PhIO and NaClO. Our results showed that the use of T(p-NO2)PPFeCl with PhI(OAc)2 as the oxidant in the presence of water displays remarkable activity for the desired oxidation reaction. The generality of this method was examined by synthesizing the carboxylic acids of pyridines and quinolines.

journal_name

Bioorg Med Chem Lett

authors

Zhong QD,Xue YZ,Yan H,Song XQ,Zhong RG

doi

10.1016/j.bmcl.2010.07.071

subject

Has Abstract

pub_date

2010-09-15 00:00:00

pages

5532-5

issue

18

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(10)01027-9

journal_volume

20

pub_type

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