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Issue 4, 2015
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Iridium(i) PNP complexes in the sp3 C–H bond activation of methyl propanoate and related esters

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Abstract

The utilisation of the PNP iridium pincer complex [Ir(PNP)(COE)][BF4] [PNP = 2,6-bis{(di-tert-butylphosphino)methyl}pyridine; COE = cyclooctene] in the sp3 C–H activation of methyl propanoate and other related esters was explored. In particular, this study provides further insight into the factors that govern the regioselectivity of such reactions. These included factors such as the steric demands of the substrate, the formation of favourable ring systems as well as the electronic effects that may influence the pKa values of protons. In particular, the effects of water on the outcome of these reactions were of great interest, since earlier literature reports have shown the presence of water to promote selective C–H activation in the α-position of ketones.

Graphical abstract: Iridium(i) PNP complexes in the sp3 C–H bond activation of methyl propanoate and related esters

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Supplementary files

Article information


Submitted
17 Sep 2014
Accepted
21 Nov 2014
First published
08 Dec 2014

Dalton Trans., 2015,44, 1585-1591
Article type
Paper
Author version available

Iridium(I) PNP complexes in the sp3 C–H bond activation of methyl propanoate and related esters

J. Coetzee, G. R. Eastham, A. M. Z. Slawin and D. J. Cole-Hamilton, Dalton Trans., 2015, 44, 1585
DOI: 10.1039/C4DT02859G

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