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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-catalyzed selective assembly of carbamoylated indoles and aminophenanthridinones via β-carbon elimination
Bo-Sheng Zhang1, Yi-Ming Wang2, Jun-Shi Zhou2
1College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, China. zhangbsh@nwnu.edu.cn.
Abstract:
Palladium-catalyzed switchable β-carbon elimination to extrude norbornene for selective synthesis of different heterocyclic skeletons is a long-standing challenge. Herein, we describe the switchable chemoselective synthesis of biologically active C4-carbamoylated indoles and C10-aminophenanthridinones by controlling β-carbon elimination, using chlorocarbamates as C-H carbamoylation reagents. Among them, C4-carbamoylated indoles are used for the synthesis of M2 receptor antagonists and p38α inhibitors. Mechanistic studies show that when β-carbon elimination is inhibited, the catalytic cycle goes through C-N bond coupling and retro-Diels-Alder reaction to generate C4-carbamoylated indoles. Alternatively, when β-carbon elimination to extrude norbornene occurs, an intramolecular C-H arylation cyclization reaction generates C10-aminophenanthridinones.
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