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.

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