With the aim at synthesizing novel allyl complexes that can potentially act as catalysts in the Tsuji-Trost catalyzed reaction, we have synthesized and characterized some allyl and 2-Meallyl palladium derivatives with one hemilabile bidentate or two strong mono-coordinating spectator ligands. The hemilabile ligands are constituted by one nitrogen heterocyclic carbene (NHC) fragment acting as the pivot bearing a labile wing with a pyridine nitrogen or sulfur atom as the second stabilizing atom. One of two monodentate ligands is in all cases PPh3 whereas the other is a mono- or partially coordinated hemilabile carbene. The complexes were characterized by standard spectroscopic methods and elemental analysis and in two cases by SC-XRD technique.The reactivity of two selected complexes toward the Tsuji-Trost reaction was tested by stoichiometric allyl amination carried out with piperidine and the results of such a mechanistic investigation integrated by a computational study are also reported in this paper. (C) 2016 Elsevier Ltd. All rights reserved.
Synthesis, characterization and a reactivity study of some allyl palladium complexes bearing bidentate hemi-labile carbene or mixed carbene/PPh3 ligands
CANOVESE, Luciano;VISENTIN, Fabiano;SCATTOLIN, THOMAS;SANTO, Claudio;
2016-01-01
Abstract
With the aim at synthesizing novel allyl complexes that can potentially act as catalysts in the Tsuji-Trost catalyzed reaction, we have synthesized and characterized some allyl and 2-Meallyl palladium derivatives with one hemilabile bidentate or two strong mono-coordinating spectator ligands. The hemilabile ligands are constituted by one nitrogen heterocyclic carbene (NHC) fragment acting as the pivot bearing a labile wing with a pyridine nitrogen or sulfur atom as the second stabilizing atom. One of two monodentate ligands is in all cases PPh3 whereas the other is a mono- or partially coordinated hemilabile carbene. The complexes were characterized by standard spectroscopic methods and elemental analysis and in two cases by SC-XRD technique.The reactivity of two selected complexes toward the Tsuji-Trost reaction was tested by stoichiometric allyl amination carried out with piperidine and the results of such a mechanistic investigation integrated by a computational study are also reported in this paper. (C) 2016 Elsevier Ltd. All rights reserved.File | Dimensione | Formato | |
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