Enantioselective C−H Borylation for the Synthesis of Axially Chiral N-Aryl Phthalimides

Axially chiral compounds with a rotation restricted N−C bond are of great importance in synthetic chemistry, pharmaceuticals, and material sciences. The search for efficient and selective routes for the synthesis of these frameworks is of great interest and importance. We herein disclose an iridium-catalyzed asymmetric C−H borylation protocol for the enantioselective synthesis of chiral N-aryl phthalimides. The current method features good compatibility of functional groups, broad substrate scope, and high enantioselectivities. We also demonstrate the synthetic utility on a gram-scale C−H borylation for diverse C−B bond transformations, including the preparation of a chiral catalyst for asymmetric catalysis.