Cyclopalladiated aromatic imines in organic synthesis: the preparation of cinnamonitriles, cinnamates, unsymmetrical stilbenes, isoquinolones, and isoquinolines
Abstract
The preparation and characterisation of some new ortho-palladiated benzaldimine complexes and their reaction with olefins are described. The reaction of di-µ-1-chloro-bis(2-alkyl-2,1-benzazapalladole) complexes (1) with styrene in trifluoroacetic acid–acetic acid mixtures yielded stilbene-2-carbaldehydes (10). These were converted into 2-methyl-3-phenyl-1(2H)-isoquinolones (12)via a mercury(II) mediated cyclisation of the N-methylimine derivatives of the stilbenes. Reaction of the complexes (1) with methyl acrylate produced methyl 2-(N-t-butyliminomethyl)cinnamates (7; Y = CO2Me) and with acrylonitrile, the 2-(N-t-butyliminomethyl)cinnamonitriles (7; Y = CN), which upon in situ thermolysis gave the corresponding Isoquinolines (8).
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