Carboxylate-assisted C-H activation of phenylpyridines with copper, palladium and ruthenium: a mass spectrometry and DFT study

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F15%3A10311963" target="_blank" >RIV/00216208:11310/15:10311963 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1039/c5sc01729g" target="_blank" >http://dx.doi.org/10.1039/c5sc01729g</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c5sc01729g" target="_blank" >10.1039/c5sc01729g</a>

Result language
angličtina
Original language name
Carboxylate-assisted C-H activation of phenylpyridines with copper, palladium and ruthenium: a mass spectrometry and DFT study
Original language description
The C-H activation of 2-phenylpyridine, catalyzed by copper(II), palladium(II) and ruthenium(II) carboxylates, was studied in the gas phase. ESI-MS, infrared multiphoton dissociation spectroscopy and quantum chemical calculations were combined to investigate the intermediate species in the reaction. Collision induced dissociation (CID) experiments and DFT calculations allowed estimation of the energy required for this C-H activation step and the subsequent acetic acid loss. Hammett plots constructed from the CID experiments using different copper carboxylates as catalysts revealed that the use of stronger acids accelerates the C-H activation step. The reasoning can be traced from the associated transition structures that suggest a concerted mechanism and the key effect of the carbon-metal bond preformation. Carboxylates derived from stronger acids make the metal atom more electrophilic and therefore shift the reaction towards the formation of C-H activated products.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
<a href="/en/project/GA14-20077S" target="_blank" >GA14-20077S: Non-heme iron catalysts: Investigation of reaction mechanisms</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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