Jump to main content
Jump to site search

Issue 10, 2013
Previous Article Next Article

Selective activation of secondary C–H bonds by an iron catalyst: insights into possibilities created by the use of a carboxyl-containing bipyridine ligand

Author affiliations

Abstract

In this work, we report the discovery of a carboxyl-containing iron catalyst 1 (FeII-DCBPY, DCBPY = 2,2′-bipyridine-4,4′-dicarboxylic acid), which could activate the C–H bonds of cycloalkanes with high secondary (2°) C–H bond selectivity. A turnover number (TN) of 11.8 and a 30% yield (based on the H2O2 oxidant) were achieved during the catalytic oxidation of cyclohexane by 1 under irradiation with visible light. For the transformation of cycloalkanes and bicyclic decalins with both 2° and tertiary (3°) C–H bonds, 1 always preferred to oxidise the 2° C–H bonds to the corresponding ketone and alcohol products; the 2°/3° ratio ranged between 78/22 and >99/1 across 7 examples. 18O isotope labelling experiments, ESR experiments, a PPh3 method and the catalase method were used to characterize the reaction process during the oxidation. The success of 1 showed that, in addition to using a bulky catalyst, high 2° C–H bond selectivity could also be achieved using a less bulky molecular iron complex as the catalyst.

Graphical abstract: Selective activation of secondary C–H bonds by an iron catalyst: insights into possibilities created by the use of a carboxyl-containing bipyridine ligand

Back to tab navigation

Supplementary files

Article information


Submitted
18 Jun 2013
Accepted
02 Aug 2013
First published
07 Aug 2013

New J. Chem., 2013,37, 3267-3273
Article type
Paper

Selective activation of secondary C–H bonds by an iron catalyst: insights into possibilities created by the use of a carboxyl-containing bipyridine ligand

S. Cheng, J. Li, X. Yu, C. Chen, H. Ji, W. Ma and J. Zhao, New J. Chem., 2013, 37, 3267
DOI: 10.1039/C3NJ00656E

Social activity

Search articles by author

Spotlight

Advertisements