N-Heterocyclic Pyridylmethylamines: Synthesis, Complexation, Molecular Structure, and Application to Asymmetric Suzuki–Miyaura and Oxidative Coupling Reactions
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
10.1021/om200375s.s002
https://acs.figshare.com/articles/journal_contribution/N_Heterocyclic_Pyridylmethylamines_Synthesis_Complexation_Molecular_Structure_and_Application_to_Asymmetric_Suzuki_Miyaura_and_Oxidative_Coupling_Reactions/2625250
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 <i>N</i>,<i>N</i>-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%.
2011-08-08 00:00:00
characterization
ee
solution
Application
Pyridylmethylamine
Suzuki
ligand
Asymmetric
Complexation
Oxidative
oxidative naphthol
core
combination
Molecular Structure
enantioselectivitie
pyridylmethylamine
yield
preparation
methoxybinaphthyl derivatives
ReactionsThe synthesis
Pd complexes
cuprous iodide
Synthesi