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Bisphosphine ligands, metallamacrocycles and a solid-supported alkene metathesis catalyst

Authors: Nichols, David Andrew;

Bisphosphine ligands, metallamacrocycles and a solid-supported alkene metathesis catalyst

Abstract

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.

Country
United Kingdom
Related Organizations
Keywords

QH345 Biochemistry, Metathesis (chemistry), ligands (biochemistry), transition metal catalysts., QD Chemistry, 540

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
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