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; D.J. Cole-Hamilton

doi:10.1039/c4dt02859g

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, D.J. Cole-Hamilton

Research output: Contribution to journal › Article › peer-review

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 pK_a 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.

Original language	English
Pages (from-to)	1585-1591
Number of pages	7
Journal	Dalton Transactions
Volume	44
Issue number	4
Early online date	8 Dec 2014
DOIs	https://doi.org/10.1039/c4dt02859g
Publication status	Published - 28 Jan 2015

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Copyright © 2014 The Author(s). This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1039/C4DT02859G
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Cite this

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title = "Iridium(I) PNP complexes in the sp3 C-H bond activation of methyl propanoate and related esters",

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.",

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T1 - Iridium(I) PNP complexes in the sp3 C-H bond activation of methyl propanoate and related esters

AU - Coetzee, J.

AU - Eastham, G.R.

AU - Slawin, A.M.Z.

AU - Cole-Hamilton, D.J.

PY - 2015/1/28

Y1 - 2015/1/28

N2 - 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.

AB - 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.

UR - http://www.rsc.org/suppdata/dt/c4/c4dt02859g/c4dt02859g1.pdf

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SP - 1585

EP - 1591

JO - Dalton Transactions

JF - Dalton Transactions

IS - 4

ER -

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

Abstract

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