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Updated: Dec 27, 2025

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Palladium(0)/benzoic acid catalysis merges sequences with D2O-promoted labelling of C-H bonds
Gianpiero Cera1, Nicola Della Ca'1, Giovanni Maestri1
1Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale , Università di Parma , Parco Area delle Scienze 17/A , 43124 Parma , Italy .
Abstract:
The combination of a Pd(0) complex with benzoic acid in the presence of D2O enables the synthesis of valuable families of highly deuterated organics through elaborate sequential reactions. The catalytic system can convert 2-butyne fragments into the corresponding d-dienamides, which can then readily deliver labeled polycyclic quinone motifs. Propargylated tryptamines lead to formation of highly enriched tetrahydrocarbolines through the C-H activation of their unprotected indole ring. Mechanistic studies reveal the ordered series of events that regulate the outcome of these complex reactions, which include multiple, sequential and selective H/D scrambling from the cheapest and safest deuterium source.
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