
The aim of this work was to develop a solid-supported alkene metathesis catalyst. The initial strategy involved two new bisphosphine ligands, DPEN I and DPPN II, and the short and efficient syntheses of these ligands from 2,7-dihydroxynaphthalene are described. The platinum, palladium and ruthenium complexes of ligands I and II were investigated. The ligands were found to favour bridging metal centres to form dimeric or oligomeric complexes. The isolation and structures of three metallamacrocycles formed with platinum(II) are discussed. It was found that the thermodynamically favoured structures were the cis, cis-dimers and that isomerisation to these was catalysed by excess ligand. The bisphosphine ligands were not suitable for use in a solid-supported metathesis N-heterocyclic carbene ligand. The synthesis of bis-mesityl diamine III from L-tyrosine methyl ester is described. Diamine III was immobilised on polystyrene resin and then converted to metathesis catalyst IV. The extensive optimisation carried out in the solid phase synthesis of IV is discussed. A number of diene substrates were synthesised and the supported catalyst was tested for ring closing metathesis activity with good results. However, no enantioselectivity was observed when using the catalyst for RCM of prochiral trienes.
QH345 Biochemistry, Metathesis (chemistry), ligands (biochemistry), transition metal catalysts., QD Chemistry, 540
QH345 Biochemistry, Metathesis (chemistry), ligands (biochemistry), transition metal catalysts., QD Chemistry, 540
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