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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

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.
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https://hal.univ-brest.fr/hal-01580466
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Submitted on : Friday, September 1, 2017 - 3:36:00 PM
Last modification on : Thursday, December 9, 2021 - 3:54:03 PM

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Alexander Betz, Lian Yu, Markus Reiher, Annie-Claude Gaumont, Paul-Alain Jaffres, et al.. (N,N) vs. (N,S) chelation of palladium in asymmetric allylic substitution using bis(thiazoline) ligands: A theoretical and experimental study. Journal of Organometallic Chemistry, Elsevier, 2008, 693 (15), pp.2499 - 2508. ⟨10.1016/j.jorganchem.2008.04.044⟩. ⟨hal-01580466⟩

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