Helvetica Chimica Acta p. 2531 - 2537 (1992)
Update date:2022-07-30
Topics: Column chromatography Kinetic studies X-ray crystallography Chelation Steric Effects Electronic effects C–H Activation Yield calculation Cyclopalladation Schlenk technique NMR spectroscopy (1H, 13C)
Mossi, Waldo
Klaus, Alfred J.
Rys, Paul
The cyclopalladation of two different types of aniline derivatives is described: the acetylated anilines N-(3-methylphenyl)acetamide (2a), 3-(acetylamino)-4-chlorobenzoic acid (2c), and N-(2-chlorophenyl)acetamide (2d) are cyclometalated easily with palladium(II) acetate and trifluoroacetic acid to yield the corresponding complexes 4a, 4c, and 4d, respectively, whereas the acetylated meta-toluidine N-(2-chloro-5-methylphenyl)acetamide (2b) cannot be metalated at the only accessible site between the acetylamino and the methyl group.This aromatic C-H bond can be activated, however, with the second type of meta-toluidine derivatives: the 2-chloro-5,N-dimethyl-N-nitrosoaniline (3b) readily undergoes cyclopalladation to yield the corresponding Pd(II) complex di-μ-trifluoroacetato-bis<3-chloro-6-methyl-2-(N-methyl-N-nitrosamino)phenyl-C,N=O>dipalladium(II) (5b) containing a five-membered palladacylce with coordination of Pd(II) at the nitroso N-atom, which is established by 15N-NMR spectroscopy.
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