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The Pd?sigma-alkyl complex 5, is stable in solution for long periods in the absence of base. On addition of simple amine bases, such as 1,8-bis(dimethylamino)naphthalene (7), complex 5 rapidly generates the triene 6 via a beta-H elimination process whose stereochemistry is demonstrated to be syn. In contrast to the low primary kinetic isotope effects (kH/kD) that normally attend syn-beta-H elimination processes from sigma-alkylmetal species, large values are observed on performing inter- and intramolecular competition experiments with 5. However, the substitution of D for H has negligible effect on the absolute rate at low temperatures (?60 C). A mechanism to account for this behavior is presented, and implications for asymmetric Heck reactions are noted. Copyright
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Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate