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Issue 62, 2019
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Intramolecular palladium(II)/(IV) catalysed C(sp3)–H arylation of tertiary aldehydes using a transient imine directing group

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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.

Graphical abstract: Intramolecular palladium(ii)/(iv) catalysed C(sp3)–H arylation of tertiary aldehydes using a transient imine directing group

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Publication details

The article was received on 11 May 2019, accepted on 04 Jul 2019 and first published on 08 Jul 2019


Article type: Communication
DOI: 10.1039/C9CC03644J
Chem. Commun., 2019,55, 9172-9175

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    Intramolecular palladium(II)/(IV) catalysed C(sp3)–H arylation of tertiary aldehydes using a transient imine directing group

    S. St John-Campbell and J. A. Bull, Chem. Commun., 2019, 55, 9172
    DOI: 10.1039/C9CC03644J

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