Reactions of Cyclopalladated Compounds. Part 21. Various Examples of Sulphur-assisted Intramolecular Palladation of Aryl and Alkyl Groups

DOI: 10.1039/DT9890001715

Source and publish data:

Journal of the Chemical Society, Dalton Transactions p. 1715 - 1720 (1989)

Update date:2022-08-02

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Authors:

Dupont, Jairton

Beydoun, Nohma

Pfeffer, Michel

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Article abstract of DOI:10.1039/DT9890001715

The cyclopalladation reactions of several sulphur-containing ligands have been investigated.The thioethers benzyl methyl sulphide, methyl naphthyl sulphide, 2,6-dimethylphenyl methyl sulphide, and neopentyl sulphide have been metallated by palladium acetate in acetic acid at either aryl or alkyl carbon atoms to afford, after reaction with lithium chloride in acetone, dimeric chloride-bridged cyclopalladated complexes in moderate (22percent) to good (81percent) yields.In these products each metal is part of a five-membered ring.The same reaction with 2-biphenyl methyl sulphide afforded a dimeric complex containing a six-membered cyclopalladated ring through palladation of the ortho position of the biphenyl group. 4,4'-Dimethoxythiobenzophenone and N,N,N',N'-tetramethyl-thiourea have been palladated by using a ligand-exchange reaction with <2> in the presence of stoicheiometric amounts of trifluoroacetic acid.This afforded good yields of dimeric palladocyclic complexes through the metallation of a carbon ortho to the thioketone, or of a methyl group of the thiourea, respectively.With 1,3-bis(methylthiomethyl)benzene this latter reaction, by metallation on the 2 position of the aryl ring, afforded excellent yields of a monomeric compound in which both sulphur atoms are co-ordinated to the palladium centre.

Full text of DOI:10.1039/DT9890001715

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