Title A DFT study of site-selectivity in oxidative addition reactions with $Pd^{0}$ complexes: the effect of an azine nitrogen and the use of different types of halogen atoms in the substrateA DFT study of site-selectivity in oxidative addition reactions with $Pd^{0}$ complexes: the effect of an azine nitrogen and the use of different types of halogen atoms in the substrate Author Herrebout, Wouter A. Nagels, Nick Verbeeck, Stefan van der Veken, Benjamin J. Maes, Bert U.W. Faculty/Department Faculty of Sciences. Chemistry Research group Organic synthesis Molecular Spectroscopy Publication type article Publication 2010Weinheim, 2010 Subject Chemistry Source (journal) European journal of organic chemistry. - Weinheim Volume/pages (2010):16, p. 3152-3158 ISSN 1434-193X ISI 000278888700016 Carrier E Target language English (eng) Full text (Publishers DOI) Affiliation University of Antwerp Abstract The site-selectivity of Pd-catalyzed reactions of 2,3-dihalopyridines [2,3-dichloropyridine (1), 2,3-dibromopyridine (3) and 2-chloro-3-iodopyridine (2)] has been studied by computing the oxidative addition process using DFT calculations. The activating effect of the azine nitrogen atom on C(2) and C(3) has been obtained by comparison with the corresponding dihalobenzene [1,2-dichlorobenzene (4), 1,2-dibromobenzene (5) and 1-chloro-2-iodobenzene (6)]. The performed calculations involve the use of Pd(PPh3)2, Pd(BINAP) and Pd(XANTPHOS) as catalysts. The formation of pre-reactive complexes proved to be a very important factor in the determination of the activation energy values. A comparison with the simplified systems Pd(PPH3)2, Pd(H-BINAP) and Pd(HXANTPHOS) revealed that care has to be taken when simplified catalyst systems are used for the simulation of the oxidative addition process. E-info https://repository.uantwerpen.be/docman/iruaauth/00025b/2206fff2d1a.pdf http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000278888700016&DestLinkType=RelatedRecords&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000278888700016&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000278888700016&DestLinkType=CitingArticles&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848 Handle