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Grubbs Group - Professor Product Portal

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Professor Phil S Baran Professor Robert H. Grubbs

Research in the Grubbs group has centered on the development and application of a suite of highly active, selective, and bench stable ruthenium alkylidene complexes capable of catalyzing versatile olefin metatheses. Most notably, access to monodisperse polymers and macrocyclic/linear small molecules has been enabled through the use of these precatalysts. The ligands on ruthenium include, but are not limited to, neutral phosphines, N-heterocyclic carbenes, and pyridyl moieties, which allow for manipulations of initiation and/or propagation activity, stability, and selectivity. Similar accomplishments have been achieved with anionic ligand variations. Traditionally, olefin metathesis predominantly forms the thermodynamically favored (E)-olefin. Recent developments, however, which make use of cyclometallated N-heterocyclic carbene ruthenium alkylidene complexes, have unveiled a catalyst that forms (Z)-olefins almost exclusively. Advances in metathesis catalysts in the Grubbs group have had ubiquitous applications in the fields of energy, materials, pharmaceuticals, and natural product total synthesis.


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Products available at Aldrich from the Grubbs Laboratory

     

Adam M Johns, Tonia S Ahmed, Bradford W Jackson, Robert H Grubbs, Richard L Pederson
Organic Letters 2016-02-19
The first kinetically controlled, highly trans-selective (>98%) olefin cross-metathesis reaction is demonstrated using Ru-based catalysts. Reactions with either trans or cis olefins afford products with highly trans or cis stereochemistry, respectively. This E-selective olefin cross-metathesis is shown to occur between two trans...Read More
Peter K Dornan, Zachary K Wickens, Robert H Grubbs
Angewandte Chemie. International edition in English 2015-06-08
A stereoselective synthesis of anti-1,2-diols has been developed using a multitasking Ru catalyst in an assisted tandem catalysis protocol. A cyclometalated Ru complex catalyzes first a Z-selective cross-metathesis of two terminal olefins, followed by a stereospecific dihydroxylation. Both steps are catalyzed by Ru, as the Ru co...Read More
Keary M Engle, Gang Lu, Shao-Xiong Luo, Lawrence M Henling, Michael K Takase, Peng Liu, K N Houk, Robert H Grubbs
Journal of the American Chemical Society 2015-05-06
A series of second-generation ruthenium olefin metathesis catalysts was investigated using a combination of reaction kinetics, X-ray crystallography, NMR spectroscopy, and DFT calculations in order to determine the relationship between the structure of the chelating o-alkoxybenzylidene and the observed initiation rate. Included ...Read More
Myles B Herbert, Robert H Grubbs
Angewandte Chemie. International edition in English 2015-04-20
Olefin cross metathesis is a particularly powerful transformation that has been exploited extensively for the formation of complex products. Until recently, however, constructing Z-olefins using this methodology was not possible. With the discovery and development of three families of ruthenium-based Z-selective catalysts, the f...Read More
Vanessa M Marx, Alexandra H Sullivan, Mohand Melaimi, Scott C Virgil, Benjamin K Keitz, David S Weinberger, Guy Bertrand, Robert H Grubbs
Angewandte Chemie. International edition in English 2015-02-02
An expanded family of ruthenium-based metathesis catalysts bearing cyclic alkyl amino carbene (CAAC) ligands was prepared. These catalysts exhibited exceptional activity in the ethenolysis of the seed-oil derivative methyl oleate. In many cases, catalyst turnover numbers (TONs) of more than 100,000 were achieved, at a catalyst l...Read More