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

ABSTRACT: Simple amine and diamine derivatives can promote the palladium catalysed direct ?-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.

SUBMITTER: St John-Campbell S

PROVIDER: S-EPMC5603794 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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

St John-Campbell S S White A J P AJP Bull J A JA

Chemical science 20170504 7

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 ...[more]

PMID: 28959406

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