Olefin Metathesis at the 250th ACS Meeting

The 250th ACS National Meeting & Exposition is set for the history-rich city of Boston, MA from August 16 – 20, 2015. The theme of the event is “Innovation from Discovery to Application” which fits well with our favorite topic of olefin metathesis, and is something that we do here at Materia on a daily basis as we investigate new applications where olefin metathesis can supply innovative solutions to challenging problems. As we do before every ACS National Meeting, we’ll provide an overview of some of the interesting talks and poster presentations that caught our eye while scanning the technical program.

First off, I always like to start with what our Nobel Laureates have planned. Prof. Richard Schrock from MIT is scheduled to give one presentation. His talk (PMSE 80) is titled “Stereospecific polymerization of cyclic olefins through ROMP” and is set for Monday Aug. 17th at 8:30 a.m. Prof. Bob Grubbs from Caltech will present a total of 5 talks, 2 of which will focus on the science and 3 from more of a business angle that truly highlights the meeting theme of innovation from discovery to application:

  • PMSE 11 – Ring opening metathesis polymerization (ROMP) in the synthesis of precise polymer structures and commercial applications
  • PMSE 81 – Design and applications of olefin metathesis catalysts for precise structural control
  • SCHB 17 – Olefin metathesis chemistry as a catalyst for building businesses BRIC by BRIC
  • SCHB 20 – Olefin metathesis for commercial development of polymers on a commercial scale
  • CHED 380 – Fundamental research to commercial products

The Schrock and Grubbs laboratories are also scheduled to contribute in Boston. From the Schrock group, there are 3 poster presentations describing different research projects including silica-supported W-oxo alklyidenes for tandem alkane metathesis (INOR-574); kinetic studies of alternating trans-AB copolymers using Mo-based catalysts (INOR-575); and the use of Mo-imido catalysts for the preparation of haloalkenes (INOR-788). From the Grubbs’ group, Tonia Ahmed will present a poster describing Z-to-E isomerization processes when cyclometalated Z-selective Ru-alkylidenes are employed (INOR-576) and presentation INOR-239 will describe NHC metal complexes with fluorinated NHC backbones in a collaborative contribution between the Grubbs group and the United States Air Force.

Heterogeneous catalysis has always been a research topic that I’ve been drawn to. The Division of Catalysis Science and Technology has a couple talks that look particularly interesting – first on Sunday, Aug. 16th at 8:05 a.m., Prof. Omar Yaghi will discuss the use of functionalized MOFs as a means to immobilize catalysts (CATL-16). A specific example that he will discuss will involve the use of a Ru-catecholate olefin metathesis catalyst and the improved properties of the immobilized system. Secondly, a related talk will be given on Monday, Aug. 17th at 9:05 a.m. from the Van Bokhoven lab at ETH Zurich and the Paul Scherrer Institute that will describe the use of phosphine functionalized MOFs (CATL-89). Again, the author will describe an olefin metathesis example employing the Grubbs Catalyst® 2nd Generation.

Finally, I’ll provide a list of presentations that also jumped out at me when searching the technical program.

Monday, August 17th

  • PMSE-79 – Synthesis of functionalized oligomers by ROMP and their hydrogenation, presented by Renat Kadyrov @ 8 a.m.
  • PMSE-82 – (Imido)vanadium(V) complex catalysts for olefin insertion/metathesis polymerization, presented by Kotohiro Nomura @ 9:30 a.m.
  • POLY-145 – Stereo- and regioregular ring opening metathesis polymerization and cyclopolymerization of cyclic olefins and diynes containing protic functional groups by functional group-tolerant Mo- and W-based metathesis catalysts, presented by Michael Buchmeiser @ 2:40 p.m.

Tuesday, August 18th

  • INOR-469 – Molybdenum and tungsten imido alkylidene N-heterocyclic carbene complexes: Activity, immobilization, and functional group tolerance in olefin metathesis, presented by Michael Buchmeiser @ 2:10 p.m.

Wednesday, August 19th

  • ORGN-603 – Mechanochemical ruthenium-catalyzed olefin metathesis: From small molecules to polymers, presented by Louis Do @ 10:40 a.m.
  • ORGN-622 – Fluorous Grubbs metathesis catalysts: Applications in phase transfer activation, presented by Hassan Bazzi @ 2:20 p.m.

Thursday, August 20th

  • CARB-133 – Imparting functional variety to cellulose ethers via olefin cross-metathesis, presented by Yifan Dong @ 11:15 a.m.
  • POLY-499 – Milling toward polymers: Solvent-free, Ru-catalyzed mechanochemical olefin metathesis polymerizations, presented by Louis Do @ 2:40 p.m.

Lastly, after being unable to attend the spring show in Denver, Materia representatives will be back in full force in Boston. Please stop by Booth #1211 to learn a little bit about the exciting field of olefin metathesis. You can take our Metathesis Challenge and then head home with a hip Materia T-shirt that will cause jealousy amongst your peers! (While supply lasts) See you on the East Coast!!

Controlling the “Light” Path to Metathesis

fig1-chromatically-orthogonal-reagents

Levin, E.; Mavila, S.; Eivgi, O.; Tzur, E.; Lemcoff, N.G. “Regioselective Chromatic Orthogonality with Light-Activated Metathesis Catalysts” Angew. Chem. Int. Ed. 2015, Advance Article. DOI: 10.1002/anie.201500740 The control of molecular bond … [Continue reading]

Olefin Metathesis in Self-Healing Materials

ATM self healing

Neal, J. A.; Mozhdehi, D.; Guan, Z. “Enhancing Mechanical Performance of a Covalent Self-Healing Material by Sacrificial Noncovalent Bonds” J. Am. Chem. Soc. 2015, 137, 4846-4850. Self-healing materials have been an objective of extensive research … [Continue reading]

New Remarkably Efficient Ethenolysis Catalysts

ethenolysis-1

Marx, V. M.; Sullivan, A. H.; Melaimi, M.; Virgil; S. C.; Keitz, B. K.; Weinberger, D. S.; Bertrand, G. and Grubbs, R. H. “Cyclic Alkyl Amino Carbene (CAAC) Ruthenium Complexes as Remarkably Active Catalysts for Ethenolysis” Angew. Chem. Int. Ed. … [Continue reading]

Olefin Metathesis at the 249th ACS Meeting

The 249th ACS National Meeting & Exposition is fast approaching with Denver, CO preparing to host the biannual event from March 22 – 26, 2015. The theme of this spring’s event is “Chemistry of Natural Resources” which is fitting for the … [Continue reading]

Yves Chauvin, One of Metathesis Greats, Dies at 84

Yves Chauvin, one of the “metathesis greats,” passed away on January 27, 2015 at the age of 84. Winner of the Nobel Prize in Chemistry in 2005, Chauvin was a key player in proposing the metallacyclobutane intermediate of the generally accepted … [Continue reading]

The Boomerang is Back in Olefin Metathesis

Boomerang

Bates, J. M.; Lummiss, J. A. M.; C.; Bailey; G. A., and Fogg, D. E. “Operation of the Boomerang Mechanism in Olefin Metathesis Reactions Promoted by the Second-Generation Hoveyda Catalyst” ACS Catal., 2014, 4 (7), 2387-94. No consensus has been … [Continue reading]

Olefin Metathesis at the 248th ACS Meeting

The 248th American Chemical Society National Meeting and Exposition will be held in San Francisco, California from August 10-14, 2014. The theme of this fall’s meeting is “Chemistry and Global Stewardship.” As olefin metathesis has made significant … [Continue reading]

Examining Polytopal Rearrangements around Ruthenium

fig_1r

Torker, S.; Khan, R.K.M.; Hoveyda, A.M. “The Influence of Anionic Ligands on Stereoisomerism of Ru Carbenes and Their Importance to Efficiency and Selectivity of Catalytic Olefin Metathesis Reactions” J. Am. Chem. Soc. 2014, 136, 3439-3455. For … [Continue reading]