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Updated: Jan 11, 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(II)-Catalyzed [3 + 2] Annulation of Aromatic Triflamides via Maleimide-Relayed Dual C-H Activation Process
Trisha Chakraborty1, Masilamani Jeganmohan1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu 600036, India.
Abstract:
A palladium-catalyzed [3 + 2] annulation of substituted aromatic triflamides with maleimides affording tricyclic heterocycles bearing a free NHTf group in a highly atom- and step-economical manner has been developed. Quinoxaline serves as the key ligand, facilitating sequential two-fold C-H activation: First C-H activation takes place selectively at the benzylic position, which triggers a relayed second C-H bond activation at the meta position. Furthermore, ortho-C(sp2)-H alkenylation of the annulated product has been shown exploiting the preserved NHTf group. Additionally, mechanistic studies support a plausible pathway for the annulation.
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