With applications in scales from laboratory to industrial, and in fields ranging from pharmaceuticals to materials, olefin metathesis is one of the most powerful tools available to chemists in the formation and manipulation of carbon-carbon double bonds. Supported by a variety of well-defined, stable, and adaptable Mo- and Ru-based catalyst1,2, the field of olefin metathesis has not only thrived in the past few decades but continues to show immense potential5. The methodologies surrounding olefin metathesis, however, have not deviated much from solution-based routes and mechanochemical methods have not been widely investigated to our knowledge3,4. We present solvent-free Ru-based catalysis in a ball mill as a potentially attractive and versatile alternative to traditional synthetic methods in performing olefin metathesis, namely being rapid (0.5-3hrs compared to 12-48 hrs), environmentally friendlier (substoichiometric Liquid-Assisted Grinding compared to dichloromethane, benzene, and other toxic bulk solvents), and afford desired products in good to excellent yields (73-97% isolated yields).[1] R. R. Schrock, Tetrahedron, 1999 , 55, 8141[2] M. S. Sanford, J. A. Love and R. H. Grubbs, J. Am. Chem. Soc., 2001 , 123, 6543[3] A. Piermattei, S. Karthikeyan and R. P. Sijbesma, Nature Chemistry, 2009 , 1, 133[4] L. Gulajski, Pawel Sledz, A. Lupa and K. Grela, Green Chem., 2008 , 10, 271[5] J. Hartung and R. H. Grubbs, J. Am. Chem. Soc., 2013 , 135, 10183

Solvent-free ruthenium catalysis in a ball mill: Exploring olefin metathesis from a mechanochemical perspective

248th National Meeting (2014)

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