In terms of an optimum material balance, intermolecular catalytic hydroamination reactions [Eq. (1)] are one of the much discussed atom‐economical processes. The problems of hydroamination have not yet been properly solved; however, recent publications describe some very promising work on the homogeneous catalysis of intermolecular hydroamination reactions with transition metal catalysts. This work is described and discussed herein.
The kinetics of the palladiumcatalyzed biphasic telomerization of butadiene and ammonia by means of in situ catalysts consisting of phosphane palladium complexes were investigated at 80 8C. The effects of ligand, catalyst, and ammonia concentrations were studied. The rate of product formation as well as the regioselectivity of the reaction was found to depend greatly on ligand and catalyst concentration. A model for the reaction mechanism was deduced from these results, explaining the regioselectivities obtained. The regioselectivity could be strongly influenced by the ligand. We synthesized new water-soluble phosphanes with special p-acceptor/s-donor properties for use in the telomerization reaction. TPPTS as a ligand gave the terminal octadienylamine with a regioselectivity of 50 %, whilst a TPPTS derivative with three methoxy groups in ortho positions led to a regioselectivity of 94 %. This corroborated the importance of ligand properties in this reaction.
We describe for the first time an alternative and far more efficient method to synthesise functionalised ionic liquids in a simple, straightforward, two-step synthesis.
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