Are you an EPFL student looking for a semester project?
Work with us on data science and visualisation projects, and deploy your project as an app on top of Graph Search.
Concept
Grubbs catalyst
Summary
Grubbs catalysts are a series of transition metal carbene complexes used as catalysts for olefin metathesis. They are named after Robert H. Grubbs, the chemist who supervised their synthesis. Several generations of the catalyst have also been developed. Grubbs catalysts tolerate many functional groups in the alkene substrates, are air-tolerant, and are compatible with a wide range of solvents. For these reasons, Grubbs catalysts have become popular in synthetic organic chemistry. Grubbs, together with Richard R. Schrock and Yves Chauvin, won the Nobel Prize in Chemistry in recognition of their contributions to the development of olefin metathesis.
In the 1960s, ruthenium trichloride was found to catalyze olefin metathesis. Processes were commercialized based on these discoveries. These ill-defined but highly active homogeneous catalysts remain in industrial use. The first well-defined ruthenium catalyst was reported in 1992. It was prepared from RuCl2(PPh3)4 and diphenylcyclopropene.
This initial ruthenium catalyst was followed in 1995 by what is now known as the first-generation Grubbs catalyst. It is synthesized from RuCl2(PPh3)3, phenyldiazomethane, and tricyclohexylphosphine in a one-pot synthesis.
The first-generation Grubbs catalyst was the first well-defined Ru-based catalyst. It is also important as a precursor to all other Grubbs-type catalysts.
The second-generation catalyst has the same uses in organic synthesis as the first generation catalyst, but generally with higher activity. This catalyst is stable toward moisture and air, thus is easier to handle in laboratories.
Shortly before the discovery of the second-generation Grubbs catalyst, a very similar catalyst based on an unsaturated N-heterocyclic carbene (1,3-bis(2,4,6-trimethylphenyl)imidazole) was reported independently by Nolan and Grubbs in March 1999, and by Fürstner in June of the same year.
Official source
About this result
This page is automatically generated and may contain information that is not correct, complete, up-to-date, or relevant to your search query. The same applies to every other page on this website. Please make sure to verify the information with EPFL's official sources.