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The Synthesis of Catalytic Self-
Assembled Metal Cage Complexes
Author: Indra Yudhipratama
Supervisor: Professor N. H. Williams
Submitted to the Department of Chemistry, University of Sheffield in fulfilment
for the requirement for the award of MChem in Chemistry
April 2016

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Abstract
The aim of this project was to synthesise a reversible metal cage complexes that is
capable for catalytic activity. The target metal cage complex 19 was designed based on
the bipyridyl Co(II) complex where imine functional group acts as connecting group.
The key intermediate compound of bis-aldehyde 14 was synthesised in two steps, the
formation of enamine and periodate oxidative cleavage, with overall yield of 9 %.
From the enamine synthesis, mono-enamine 20 was also formed and further
investigation was conducted to optimise the formation of 20. It was found that 4 days
reaction with 8.5 equivalents of 16 is the optimum conditions for the synthesis of 20.
Then, it was subjected to periodate reaction to give 27 which then followed for the
formation of the modified target metal complex 30. However, the isolated product from
the cage formation cannot be structurally assigned due to complex spectrum. Further
analysis is needed to confirm whether 30 is formed or not.

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Scheme 1. The proposed route for the synthesis of self-assembled metal cage complex.

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Enamine synthesis
Formation of aldehydes: oxidative cleavage of enamine
Scheme 2. Synthesis of bipyridyl carbaldehyde

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Formation metal cage complex
Scheme 3. The proposed synthetic route for metal cage complex.