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Updated: Feb 13, 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 Regioselective C-H Functionalization of Arenes Substituted by Two N-Heterocycles and Application
Da-Wei Yin1, Gang Liu1,2
1Tsinghua-Peking Center for Life Sciences, School of Life Sciences , Tsinghua University , Handian District , Beijing 100084 , P.R. China.
Abstract:
Reported herein is a Pd-catalyzed regioselective C-H activation method that is used for C-H deuteration, carbonylation, halogenation, and oxidation of arene substrates substituted by two N-heterocycles. When conducted in acetic acid (AcOH), these reactions occur at the five-membered palladacycle sites, whereas they switch to the six-membered palladacycle sites in trifluoroacetic acid (TFA). This controllable regioselective C-H activation is applied for late-stage functionalization of bioactive molecules. A mechanism study indicated that the regioselectivity is achieved by Brönsted acid-Lewis base interactions and electronic effects (in TFA) and the different kinetic stabilities of palladacycle intermediates (in AcOH).
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