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Updated: Aug 26, 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-Catalyzed Oxidant Dependent Switchable Aza-Wacker Cyclization and Oxidative Dimerization of Benzimidates
Rodney A Fernandes1, Ashvin J Gangani1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, Maharashtra, India.
Abstract:
An oxidant dependent switchable palladium-catalyzed synthesis of 1,3-oxazines and benzohydrazonates (azines) from O-homoallyl benzimidates has been developed. The reaction involved aza-Wacker-type intramolecular cyclization of O-homoallyl benzimidates with Cu(OAc)2 as oxidant under Pd-catalysis to deliver 4-methylene-1,3-oxazines, whereas dimerization of O-homoallyl benzimidates with K2S2O8 as oxidant resulted remarkably in benzohydrazonates (azines). The reaction is atom economic with an easily operational procedure for divergent synthesis of important scaffolds.
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