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(N,N) vs. (N,S) chelation of palladium in asymmetric allylic substitution using bis(thiazoline) ligands: A theoretical and experimental study |
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| Authors: | Alexander Betz Markus Reiher Annie-Claude Gaumont Mihaela Gulea |
| Institution: | a Laboratoire de Chimie Moléculaire et Thio-Organique (LCMT), ENSICAEN, Université de Caen Basse-Normandie, CNRS 6 Boulevard du Marechal Juin, 14050 Caen, France b Laboratorium für Physikalische Chemie, ETH Zurich, Wolfgang-Pauli-Str. 10, CH-8093 Zurich, Switzerland c CEMCA, UMR CNRS 6521, Faculté des Sciences et Techniques, Université de Bretagne Occidentale, 6 Av. Victor Le Gorgeu, 29238 Brest, France |
| Abstract: | New thiazoline-containing ligands including non-symmetric bis(thiazolines) and oxazoline-thiazolines were synthesized and then compared to C2-symmetric bis(thiazolines) in the palladium-catalyzed allylic substitution. The experimental results obtained in this study support the hypothesis of a competition between the (N,N) and the (N,S) palladium chelation, when sterically hindered bis(thiazolines) are used as ligands. A quantum chemical study performed on the Pd-complexes derived from three selected ligands, two C2-symmetric bis(thiazolines) and one oxazoline-thiazoline, also supports this hypothesis. |
| Keywords: | Non-symmetric bis(thiazoline) ligands Oxazoline-thiazoline ligands Asymmetric allylic substitution Palladium complexes Quantum chemical calculations |
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