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Oxygen- versus carbon-coordination of the alpha-stabilized phosphorus ylide PhP=C(H)R in palladacycles bearing secondary amines

Transition Metal Chemistry, ISSN: 0340-4285, Vol: 36, Issue: 4, Page: 363-367
2011
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The ortho-metalated complex [Pd(x){κ (C,N)-[C HCHNRR′ (Y)}] (2a-4a and 2b-3b) was prepared by refluxing in benzene equimolecular amounts of Pd(OAc) and secondary benzylamine [a, EtNHCHPh; b, t-BuNHCHPh followed by addition of excess NaCl. The reaction of the complexes [Pd(x){κ (C,N)-[CHCH NRR′ (Y)}] (2a-4a and 2b-3b) with a stoichiometric amount of PhP=C(H)COCH-4-Z (Z = Br, Ph) (ZBPPY) (1:1 molar ratio), in THF at low temperature, gives the cationic derivatives [Pd(OC(Z-4-CHC=CHPPh){κ (C,N)-[CHCHNRR′(Y)}] (5a-9a, 4b-6b, and 4b′-6b′), in which the ylide ligand is O-coordinated to the Pd(II) center and trans to the ortho-metalated C(6)H(4) group, in an "end-on carbonyl". Ortho-metallation, ylide O-coordination, and C-coordination in complexes (5a-9a, 4b-6b, and 4b′-6b′) were characterized by elemental analysis as well as various spectroscopic techniques. © 2011 Springer Science+Business Media B.V.

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