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Updated: Dec 14, 2025
Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
A Redox-Active Heterobimetallic N-Heterocyclic Carbene Based on a Bis(imino)pyrazine Ligand Scaffold
Nicolas I Regenauer1, Sven Jänner1, Hubert Wadepohl1
1Anorganisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 276, 69120, Heidelberg, Germany.
Abstract:
A new redox-active N-heterocyclic carbene (NHC) architecture is obtained using N-methylated pyrazinediimine iron complexes as precursors. The new species exhibit strong π-accepting/σ-donating properties and are able to ligate two metal centres simultaneously. The redox activity was demonstrated by the reversible chemical oxidation of a heterobimetallic Fe0 /RhI example, which affords an isolable ligand-based radical cation. The reversible redox process was then applied in the catalytic hydrosilylation of 4,4'-difluorobenzophenone, where the reaction rate could be reversibly controlled as a function of the catalyst oxidation state. The new NHC exhibits high electrophilicity and nucleophilicity, which was demonstrated in the reversible activation of alcohols and amines. The electronic structure of the resulting complexes was investigated through various spectroscopic and computational methods.
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