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Commercial Pdx(dba)y from various suppliers was found to vary considerably in appearance, homogeneity, purity, and catalytic activity. The Buchwald-Hartwig amination of 4-bromoanisole (5) with aniline (6) was established as a sensitive test reaction to probe the efficiency of Pdx(dba)y batches in catalytic transformations. The yields obtained with 17 different Pdx(dba)y batches ranged from 10% to nearly quantitative and could not be predicted reliably on the basis of any physical or spectroscopic descriptor alone. The best results in the catalytic test reaction were consistently achieved with a self-made slowly crystallized Pd2(dba)3·toluene adduct. A protocol is disclosed that allows batches of Pdx(dba)y with unsatisfactory or inconsistent performance to be converted into this reliable precatalyst.
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Reference:
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