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Updated: Oct 25, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Palladium-Catalyzed Directed Asymmetric C-H Arylation Leading to a P-Stereogenic Center
Shengzhou Jin1,2, Mohammad Khavani3, Yu Wang4
1Hubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi435002, China.
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.
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