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GRUBBS CATALYSIS: APPLICATIONS
Grubbs catalyst is a well-defined catalyst that is widely used in organic synthesis,
including olefin metathesis which is an excellent way to make difficult ring sizes
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Grubbs catalyst has a high functional-group
tolerance and is insensitive to atmospheric oxygen and moisture
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Grubbs catalyst is often used to achieve ring-opening metathesis polymerization
(ROMP) of strained cyclic olefins, olefin cross metathesis (CM) and ring closing metathesis
(RCM) of terminal olefins under a variety of reactions conditions
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This
technique has broad applications in industrial areas ranging from pharmaceuticals to
polymers
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Therefore, the
catalyst can be used for pharmaceuticals, polymers, paper industry and more
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It also lowers the cost of the
complicated multi-step industrial processes
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The catalyst also makes the reaction easier to use as it is stable under ambient
conditions
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This shows that Grubbs used
a green chemistry approach to its catalyst by reducing the potential to create hazardous
waste
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For example, an anti-cancer drug epothilone
and its derivatives were prepared by using RCM
(Fig
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Nicolaou et al reviewed the efficiency of
RCM in the total synthesis of macrocyclic lactones
and several natural products
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Grubbs catalyst used in the RCM of epothilone
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Grubbs catalyst has also been used in polymer industry
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These cracks often form deep within the structure where detection is
difficult and repair is almost impossible
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An efficient method of repairing these cracks is autonomic healing (See Appendix)
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When a crack is formed, it ruptures embedded microcapsules, which releases healing
agent into the crack plane through capillary action
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The reaction used in trials of autonomic healing is metathesis of dicyclopentadiene
with a Grubbs catalyst (Fig
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Figure B
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The ROMP reaction invokes the use of Grubbs catalyst that shows high metathesis
activity while being tolerant of a wide range of functional groups as well as oxygen and water
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B)
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S
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H
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Polymeric Materials in Organic Synthesis and
Catalysis, Buchmeiser, M
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, Ed
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Nicolaou, K
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, Bulger, P
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& Sarlah D
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Metathesis Reactions in Total Synthesis,
Angew Chem Int Ed, 44, 4490 – 4527
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C
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, Pastor J, et al
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Synthesis of Epothilones A And B
in Solid and Solution Phase, Nature, 387, 268 – 272
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M
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Metathesis Catalyst: Historical Perspective, Recent
Developments and Practical Applications, Journal of Scientific & Industrial Research, Vol 65,
957 – 965
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R
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R
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H
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(2001)
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Nature, 409, 794-797
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P
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M
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A theory of crack healing in polymers
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Appl
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52, 5953 – 5963

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