Metal-Containing Schiff Base/Sulfoxide Ligands for Pd(II)-Catalyzed Asymmetric Allylic C–H Aminations
Youka Bunno, Yuta Tsukimawashi, M. Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga
Abstract
Metal-containing Schiff base/sulfoxides were developed as chiral ligands for Pd(II)-catalyzed asymmetric intramolecular allylic C–H amination reactions. The use of metal-containing Schiff base ligands allows tuning the selectivity and reactivity of the Pd(II)-catalyst, whereby a Schiff base-Cu(II)/sulfoxide ligand in combination with Pd(OAc)2 showed the best performance. Both internal and terminal alkenes were applicable, and the C–H amination products were obtained in up to 91:9 er.
Topics & Concepts
AminationChemistrySchiff baseCatalysisSulfoxideIntramolecular forceAllylic rearrangementSelectivityLigand (biochemistry)Reactivity (psychology)Polymer chemistryMedicinal chemistryMetalCombinatorial chemistryOrganic chemistryBiochemistryMedicineAlternative medicineReceptorPathologySynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis