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Updated: Aug 20, 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 General C-N Cross-Coupling to Synthesize Heteroaryl Amines Using a Palladacyclic N-Heterocyclic Carbene Precatalyst
Ruoqian Fan1, Meiying Kuai1, Dong Lin1
1Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, 159 Longpan Road, 210037 Nanjing, China.
Abstract:
A new palladacyclic N-heterocyclic carbene precatalyst was designed by the combination of 1,3-bis(2,6-diisopropylphenyl)acenaphthoimidazol-2-ylidene (AnIPr) with an achiral 2-naphthyl-4,4-dimethyloxazoline palladacyclic fragment. Applying this precatalyst enabled a general protocol for Pd-catalyzed C-N cross-coupling reactions of challenging five- or six-membered ring heteroaryl chlorides and various heterocyclic amines. The desired aminated products, including commercial pharmaceuticals or key intermediates such as piribedil, cyprodinil, V600EBRAF inhibitor, tripelennamine, 517-β-hydroxysteroid dehydrogenase inhibitor, brexpiprazole, and sonidegib, were achieved in good to excellent yields (>61 examples, ≤99% yields).
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