A series of acyclic aminooxycarbene(AAOC)-ligated ruthenium metathesis catalysts was developed for the ethenolysis of methyl oleate and cis-cyclooctene.AAOC pro-ligands were conveniently synthesized via a one-pot and ...A series of acyclic aminooxycarbene(AAOC)-ligated ruthenium metathesis catalysts was developed for the ethenolysis of methyl oleate and cis-cyclooctene.AAOC pro-ligands were conveniently synthesized via a one-pot and multigram-scale reaction,and the resulting AAOC–Ru catalysts exhibited outstanding catalytic efficiencies(turnover numbers(TONs)of 100000 for methyl oleate and 89000 for cis-cyclooctene)and excellent selectivities(up to 98%).The AAOC ligands possess an ambiphilic character,with both strongσ-donors andπ-acceptors.Notably,combining the strong donating ability and the unsymmetrical structure of AAOC ligands could contribute to the enhancement of the catalytic activity and selectivity of the ruthenium catalysts.This result represents a rare example of acyclic carbene–ruthenium catalysts demonstrating high catalytic efficiency and excellent selectivity in olefin metathesis reactions.展开更多
基金supported by the Technology Development Program to Solve Climate Changes through the National Research Foundation(NRF)funded by the Ministry of Science,ICT&Future Planning(NRF-2017M1A2A2049102)supported by“Nobel Research Project”grant of the Grubbs Center for Polymers and Catalysis funded by the GIST in 2020.The authors thank Dr Che-Sin Lee at the Gwangju Institute of Science and Technology(GIST)Central Research Facilities for elemental analysis.
文摘A series of acyclic aminooxycarbene(AAOC)-ligated ruthenium metathesis catalysts was developed for the ethenolysis of methyl oleate and cis-cyclooctene.AAOC pro-ligands were conveniently synthesized via a one-pot and multigram-scale reaction,and the resulting AAOC–Ru catalysts exhibited outstanding catalytic efficiencies(turnover numbers(TONs)of 100000 for methyl oleate and 89000 for cis-cyclooctene)and excellent selectivities(up to 98%).The AAOC ligands possess an ambiphilic character,with both strongσ-donors andπ-acceptors.Notably,combining the strong donating ability and the unsymmetrical structure of AAOC ligands could contribute to the enhancement of the catalytic activity and selectivity of the ruthenium catalysts.This result represents a rare example of acyclic carbene–ruthenium catalysts demonstrating high catalytic efficiency and excellent selectivity in olefin metathesis reactions.
