Palladium-Catalyzed Directed Asymmetric C–H Arylation Leading to a P-Stereogenic Center

Abstract

A novel -OH group-directed asymmetric catalytic C(sp2)–H arylation has been developed, enabling efficient access to P-stereogenic chiral compounds with excellent yields (up to 90%) and enantioselectivity (up to 98% ee). The success of this C–H functionalization system relies on the synergistic coordination of a phenolic hydroxyl functionality and (S)-6-oxopiperidine-2-carboxylic acid with the Pd metal center, which acts as the efficient directing group and chiral ligand. The reaction demonstrated a broad substrate scope, affording a diverse array of 30 distinct P-chiral products. The absolute configuration of the products was unambiguously confirmed via X-ray diffraction analysis. Furthermore, a plausible catalytic cycle mechanism has been proposed, which is supported by detailed experimental studies and DFT calculations.