Orthometallated Primary Amines. Part 1. Facile Preparation of the First Optically Active Cyclopalladated Primary Amines

DOI: 10.1039/DT9930003619

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Journal of the Chemical Society, Dalton Transactions p. 3619 - 3624 (1993)

Update date:2022-09-26

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Authors:

Vicente, Jose

Saura-Llamas, Isabel

Jones, Peter G.

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Article abstract of DOI:10.1039/DT9930003619

Reaction of 2> 1 with AgClO4 (1:2) gave a solution containing an orthopalladated complex 2.Addition to this solution of neutral ligands or NaBr led to isolation of the complexes >(L2)>ClO4 or <>(μ-Br)>2> 4, respectively.Reaction of 4 with PPh3 or Tl(acac) (Hacac = acetylacetone) gave >Br(PPh3)> 5 or >(acac)> 6, respectively.Complexes 1, 4 and 5 can be obtained optically pure by using (R)-(+)- or (S)-(-)-α-methylbenzylamine as starting material.The solid-state crystal structures of 3b and R-5 were determined at low temperatures.In both complexes the palladium atom adopts the usual square-planar co-ordination.The major angular distortion is associated with the small bite of the chelating ligand (80.8 and 81.2 deg, respectively).The weaker trans influence of the cod ligand in 3b accounts for ca. 0.02 Angstroem longer Pd-N and Pd-C bonds in R-5 than in 3b.Short contacts between the perchlorate anion or bromo ligand in 3b or R-5 with the amino group (N...O 3.06 or N...Br 3.41 Angstroem, respectively) probably represent hydrogen bonds.

Full text of DOI:10.1039/DT9930003619

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