Title
A DFT study of site-selectivity in oxidative addition reactions with <tex>$Pd^{0}$</tex> complexes: the effect of an azine nitrogen and the use of different types of halogen atoms in the substrate A DFT study of site-selectivity in oxidative addition reactions with <tex>$Pd^{0}$</tex> complexes: the effect of an azine nitrogen and the use of different types of halogen atoms in the substrate
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Weinheim ,
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
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