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http://hdl.handle.net/2445/127729
Title: | A Joint experimental-computational comparative study of the Pd(0)-catalysed reactions of aryl iodides and aldehydes with N, O, and S tethers |
Author: | Solé Arjó, Daniel Mariani, Francesco Fernández Cadenas, Israel |
Keywords: | Catàlisi homogènia Pal·ladi (Element químic) Compostos cíclics Compostos heterocíclics Teoria del funcional de densitat Homogeneous catalysis Palladium Cyclic compounds Heterocyclic compounds Density functionals |
Issue Date: | 18-May-2015 |
Publisher: | Wiley-VCH |
Abstract: | The influence of the heteroatom (nitrogen, oxygen, and sulfur) on the course of the palladium‐catalysed intramolecular reactions of aryl iodides and aldehydes having heteroatom‐containing tethers has been explored by an extensive experimental-computational (DFT) study. Two series of substrates were considered, namely aldehydes bearing either the α‐(2‐iodobenzylheteroatom) or β‐(2‐iodophenylheteroatom) moieties. While some experimental differences were observed when changing from nitrogen to oxygen or sulfur in the 2‐iodobenzyl series, the aldehydes in which the heteroatom is directly bonded to the aromatic ring showed common chemical behaviour regardless of the nature of the heteroatom. The different reaction pathways leading to the experimentally observed reaction products were studied by computational means. Our calculations suggest that in all cases the initial nucleophilic addition involving a σ‐aryl-PdII intermediate is preferred over the competing concerted metallation-deprotonation (CMD) process. Keywords: Homogeneous catalysis / Palladium / Cyclization / Heterocycles / Density functional calculations |
Note: | Versió postprint del document publicat a: https://doi.org/10.1002/ejoc.201500393 |
It is part of: | European Journal of Organic Chemistry, 2015, vol. 2015, num. 18, p. 3935-3942 |
URI: | http://hdl.handle.net/2445/127729 |
Related resource: | https://doi.org/10.1002/ejoc.201500393 |
ISSN: | 1434-193X |
Appears in Collections: | Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) |
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