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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Intramolecular palladium(ii)/(iv) catalysed C(sp3)-H arylation of tertiary aldehydes using a transient imine
Sahra St John-Campbell1, James A Bull
1Department of Chemistry, Imperial College London, Molecular Sciences Research Hub, White City Campus, Wood Lane, W12 0BZ, UK. j.bull@imperial.ac.uk.
Abstract:
Palladium catalysed β-C(sp3)-H activation of tertiary aldehydes using a transient imine directing group enables intramolecular arylation to form substituted indane-aldehydes. A simple amine bearing a methyl ether (2-methoxyethan-1-amine) is the optimal TDG to promote C-H activation and reaction with an unactivated proximal C-Br bond. Substituent effects are studied in the preparation of various derivatives. Preliminary mechanistic studies identify a reversible C-H activation, product inhibition and suggest that oxidative addition is the turnover limiting step.
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