Highly Active Cross-Metathesis of Tetrafluoroethylene with a Seven-Membered N-Heterocyclic-Carbene–Ruthenium Catalyst
Kenta Mori, Midori Akiyama, Ko Inada, Yutaka Imamura, Yuichiro Ishibashi, Yusuke Takahira, Kyoko Nozaki, Takashi Okazoe
Abstract
A drastic increase in catalyst turnover number (TON) was accomplished in the cross-metathesis of tetrafluoroethylene (TFE) and vinyl ethers. Under a continuous flow of TFE, catalyst Ru7, which contains a seven-membered N-heterocyclic carbene (NHC) ligand, reached a TON of 4100; this is 2 orders of magnitude higher than the highest hitherto reported value. Mechanistic studies revealed that the expanded NHC successfully destabilizes the stable intermediates with a difluorocarbene structure, which strongly promotes the reaction.
Topics & Concepts
TetrafluoroethyleneCarbeneDifluorocarbeneChemistryRutheniumMetathesisCatalysisMedicinal chemistryPolymer chemistryPhotochemistryOrganic chemistryCopolymerPolymerizationPolymerSynthetic Organic Chemistry MethodsCatalytic Cross-Coupling ReactionsOrganometallic Complex Synthesis and Catalysis