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Issue 7, 2017
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Single operation palladium catalysed C(sp3)–H functionalisation of tertiary aldehydes: investigations into transient imine directing groups

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Abstract

Simple amine and diamine derivatives can promote the palladium catalysed direct β-C–H arylation of aliphatic aldehydes via transient imine formation. Trifluoroacetate was shown to be crucial in promoting the reaction. Sub-stoichiometric quantities of simple N-tosylethylenediamine was shown to form a bidentate directing group with an imine linkage. Isolation of an unsymmetrical palladacycle has shown different potential binding modes of the secondary NTs coordinating group by single crystal X-ray diffraction analysis, suggestive of a hemilabile ligand.

Graphical abstract: Single operation palladium catalysed C(sp3)–H functionalisation of tertiary aldehydes: investigations into transient imine directing groups

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Publication details

The article was received on 17 Mar 2017, accepted on 30 Apr 2017 and first published on 04 May 2017


Article type: Edge Article
DOI: 10.1039/C7SC01218G
Citation: Chem. Sci., 2017,8, 4840-4847
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    Single operation palladium catalysed C(sp3)–H functionalisation of tertiary aldehydes: investigations into transient imine directing groups

    S. St John-Campbell, A. J. P. White and J. A. Bull, Chem. Sci., 2017, 8, 4840
    DOI: 10.1039/C7SC01218G

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