Synthesis of a class of new phosphine-oxazoline ligands and their applications in palladium-catalyzed asymmetric addition of arylboronic acids to isatins

•A class of new chiral phosphine-oxazoline ligands was prepared.•A catalytic asymmetric addition of arylboronic acids to isatins was set up.•In situ formed Pd/phosphine-oxazoline catalysts were applied to the reaction for the first time.•3-Aryl-3-hydroxyoxindoles were obtained in high yields and good enantioselectivities.•Up to 98% enantiopurity of the products was obtained after one recrystallization.

A class of new phosphine-oxazoline ligands was prepared from commercially available and inexpensive starting materials. As the first example, in situ formed catalysts generated from chiral phosphine-oxazolines and Pd(OAc)2 were successfully applied to the asymmetric addition reactions of arylboronic acids to isatins, and 3-aryl-3-hydroxyoxindoles were obtained in up to 97% yields and good enantioselectivities (up to 88% ee). Up to 98% enantiopurity of the products were obtained after one recrystallization.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (141 K)Download as PowerPoint slide