About
All Things Metathesis was developed by Materia, Inc. for the two-fold purpose of establishing a knowledge resource on olefin metathesis and providing a setting for the growing number of metathesis users to discuss the technology. In light of the company’s evolving expertise in the area of olefin metathesis, Materia is committed to educating the academic and corporate communities on the benefits and applications of this Nobel Prize winning technology. All Things Metathesis provides general information on olefin metathesis and specific information on ruthenium based metathesis catalysts.
Contributing Authors

Andy Nickel
Andy grew up in the suburbs of Philadelphia and attended Temple University as an undergraduate. In college he studied chemistry and spent his free time playing rhythm guitar in a band. One day, he skipped band practice to attend a graduate student literature seminar entitled, “Ruthenium-Catalyzed Olefin Metathesis.” Despite the teasing he received from his band mates that day, he still spends much of his time thinking about this very topic. After earning his Ph.D in 2005 from Yale University in the field of natural product synthesis, Andy worked as a medicinal chemist for 3 years before joining Materia in the summer of 2008.

Jean Baptiste Bourg
Jean-Baptiste (J-B) was born in Ambilly, France and grew up in the French Alps, where he especially enjoyed skiing. He studied chemistry in Paris, earning an engineering degree from Chimie ParisTech, and did research on ruthenium-catalyzed hydrogenation. The weather in Paris being a little too rainy, he decided to move to Riverside, California. He spent the next four years trying to isolate diradicals and carbenes, and eventually completed his Ph.D. Willing to apply his knowledge on carbene chemistry to olefin metathesis, J-B worked with Prof. Grubbs before joining Materia in fall 2008.

Paul Boothe
Paul grew up outside Pittsburgh, PA and began his chemistry career as a lab assistant for a cranky graduate student at Carnegie Mellon University, before becoming a slightly less cranky graduate student himself while obtaining his Ph.D. at the University of Southern California. After a brief stint in the classroom, he retreated to the safety of the laboratory, joining Materia in 2006.

Diana Stoianova
Diana grew up in Sofia, Bulgaria and got her Masters degree at Sofia University. After she earned her Ph.D. in organic chemistry from the University of Zurich in Switzerland she moved to the States for a post doc and never left. She ran her first metathesis reaction in Paul Hanson’s group at the University of Kansas, the reaction worked really well and everybody else in the group started doing metathesis. Diana joined Materia in the fall of 2002.

Daryl Allen
Daryl was born and raised on the east coast of Canada, in the small town of Woodstock, New Brunswick. Next was the move to the big city of Fredericton, to attend the University of New Brunswick and study chemistry. Besides chemistry, Daryl occupied his time by playing numerous sports such as baseball and hockey. To pay the bills, he worked at a local ice rink as a Zamboni driver, which is one of his main claims to fame in his native country!! After completing his Ph.D. in organometallic chemistry split between the University of New Brunswick and Queen’s University in Kingston, Ontario, Daryl moved to Pasadena, CA to work as a post doc with Prof. Grubbs and then joined Materia in the spring of 2008.
About Materia, Inc.
Materia, Inc. was founded in 1998 to commercialize olefin metathesis catalyst technology. To that end, the Company has developed an extensive intellectual property portfolio, which includes over 350 issued and pending patents (worldwide) covering not only ruthenium catalyst composition and manufacture, but also methods of using the technology to perform a wide variety of transformations and compositions of certain products.

{ 12 comments… read them below or add one }
I would like to suggest a new topic about Fluorinated Aromatic Hydrocarbons.
In 2007 we found that reaction performed in such fluorinated solvents (eg. hexafluorobenzene) improved difficult metathesis reactions.
http://www.rsc.org/publishing/journals/CC/article.asp?doi=B816567J
Currently we are working on explanation this phenomena. It is not that easy.
I would appreciate put a new topic about Fluorinated solvents on your website.
People who working in olefin metathesis (and not only) could give some nice hints and comments about this unprecedented phenomena.
Best regards
Cezary
This is definitely an interesting phenomenon, Cezary, and is a good idea for a posting. A few examples have popped up the past couple of years where perfluorinated solvents show advantages, and to my knowledge no one has yet explained why. I’m glad to hear that the Grela group is working hard on this question!
Hey guys, I just saw this reaction come out in Organic Letters today. It’s a Lawrence Williams paper, where it looks like he’s metathesizing two Type-I olefins? The interesting thing is they run the reaction over 7 days, using altogether 5 mol% while adding in 5 mg portions (41 mg total) every 24 hours. I’ve never seen such a gradual addition before and wouldn’t the catalyst die much faster than just 24 hours? Or having the small amount keep the catalyst turnover from decreasing, thus allowing metathesis to occur over the whole 24 hours?
Chris
One of the substrates is better classified as a Type II olefin due to the secondary allylic OTBS group, so the good selectivity isn’t too surprising. But the rate of catalyst addition is curious indeed. It’s also interesting that “bulk” DCM is a better solvent than DCM that was purified with an alumina purification system. Any thoughts as to why?
Hi folks,
Great job on this blog. Your posts are nicely written and cut to the chase to present some important observations.
One item of interest to me: Are you aware of any studies/reports on the effects of Ru (e.g. metathesis catalysts or their byproducts) in various bioassays– either in-vitro or cell-based screens? It’s not something I worry about too much, but it would be nice to have some definitive answers for people, particularly with regards to cellular toxicity.
Thanks!
Chris,
I haven’t come across a report of if/how metathesis catalysts interfere with bioassays. If you find one, let me know!
Andy, please can you drop me an e-mail, I have a chemistry job-related question.
Best, Tomas
Hi guys,
Nothing much to add in the way of interesting questions that you might be able to investigate, but I just wanted to let you know I’ve found this website a really good and strong resource of information for my work into RCM; not just as a collection of literature, but also as a source of practical information. Also, in general I find the articles all to be enthusiastically written – metathesis certainly is an exciting area to be involved in!
Regards,
Matt
Much thanks, Matt!
Hello again to everyone at ATM.
I put my RCM work to one side for a few months, but now I’m back on the attack to work on increasing yield through optimisation of work-up and isolation. One idea that occurred from my discussion is solid-supported ruthenium catalysts for RCM; has such an idea been entertained and investigated? I would assume it has been, but I can’t seem to find anything in the literature (apart from examples where the substrate to be ring-closed is tethered to a solid support!)
I’m open to email discussion on this!
Matt
p.s. merry christmas
Matt,
Here are a few review articles to check out regarding solid-supported olefin metathesis catalysts:
(1) Coperet, C.; Basset, J.-M. AdV. Synth. Catal. 2007, 349, 78–92.
(2) Clavier, H.; Grela, K.; Kirschning, A.; Mauduit, M.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 6786–6801.
(3) Buchmeiser, M. R. Chem. Rev. 2009, 109, 303-321.
Also, another great resource is the review article by Grubbs and Vougioukalakis:
Chem. Rev. 2010, 110, 1746-1787. This is just a great review article in general, but specifically section 10 details some supported catalyst work.
Also, feel free to check out a paper that a co-worker and I published with Grubbs a few years back:
Org. Lett. 2009, 11, 1261-1264.
Perhaps here at ATM, we should do a posting on some solid-supported catalyst work…look for that in 2012.
Thanks for the interest Matt! Best of luck with your project!
Daryl
Thanks very much Daryl – I’ll be sure to read those papers!
Matt