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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,J. A. Bull
Chemical Science Pub Date : 05/04/2017 00:00:00 , DOI:10.1039/C7SC01218G
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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