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N-Heterocyclic Pyridylmethylamines: Synthesis, Complexation, Molecular Structure, and Application to Asymmetric Suzuki–Miyaura and Oxidative Coupling Reactions

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posted on 2011-08-08, 00:00 authored by Guillaume Grach, Grégory Pieters, Aurelia Dinut, Vincent Terrasson, Raouf Medimagh, Alexandre Bridoux, Vanessa Razafimahaleo, Anne Gaucher, Sylvain Marque, Jérôme Marrot, Damien Prim, Richard Gil, José Giner Planas, Clara Viñas, Isabelle Thomas, Jean-Philippe Roblin, Yves Troin
The synthesis of N,N-bidentate ligands based on a π-deficient N-heterocyclic pyridylmethylamine core is described. The preparation and characterization of the corresponding N,N-ligand–palladium complexes in solution and the solid state are illustrated. Pd complexes showed a good yield and moderate catalytic activity (up to 40% ee) in the asymmetric Suzuki–Miyaura coupling reaction, leading to methoxybinaphthyl derivatives. The combination of N,N-pyridylmethylamines with cuprous iodide revealed effective catalytic systems in oxidative naphthol derivative coupling reactions, affording the corresponding binaphthyls in high yields and with enantioselectivities of up to 61%.

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