(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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• 作者：Alex ; er Betz ; Lian Yu ; Markus Reiher ; Annie-Claude Gaumont ; Paul-Alain Jaffrè ; s ; Mihaela Gulea
• 关键词：Non-symmetric bis(thiazoline) ligands ; Oxazoline– ; thiazoline ligands ; Asymmetric allylic substitution ; Palladium complexes ; Quantum chemical calculations
• 刊名：Journal of Organometallic Chemistry
• 出版年：2008
• 期刊代码：64_0022328x
• 类别：ch
• 出版时间：15 July 2008
• 卷：693
• 期：15
• 页码：2499-2508
• 文件大小：961 K

摘要

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.