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Cyclic Alkyl Amino Carbene (CAAC) Ruthenium Complexes as Remarkably Active Catalysts for Ethenolysis
Author(s) -
Marx Vanessa M.,
Sullivan Alexandra H.,
Melaimi Mohand,
Virgil Scott C.,
Keitz Benjamin K.,
Weinberger David S.,
Bertrand Guy,
Grubbs Robert H.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201410797
Subject(s) - carbene , catalysis , ruthenium , metathesis , alkyl , chemistry , ethylene , olefin metathesis , organic chemistry , acyclic diene metathesis , olefin fiber , salt metathesis reaction , organic synthesis , derivative (finance) , medicinal chemistry , combinatorial chemistry , polymerization , financial economics , economics , polymer
An expanded family of ruthenium‐based metathesis catalysts bearing cyclic alkyl amino carbene (CAAC) ligands was prepared. These catalysts exhibited exceptional activity in the ethenolysis of the seed‐oil derivative methyl oleate. In many cases, catalyst turnover numbers (TONs) of more than 100 000 were achieved, at a catalyst loading of only 3 ppm. Remarkably, the most active catalyst system was able to achieve a TON of 340 000, at a catalyst loading of only 1 ppm. This is the first time a series of metathesis catalysts has exhibited such high performance in cross‐metathesis reactions employing ethylene gas, with activities sufficient to render ethenolysis applicable to the industrial‐scale production of linear α‐olefins (LAOs) and other terminal‐olefin products.