Cyclic alkyl amino carbene (CAAC) ruthenium complexes as remarkably active catalysts for ethenolysis
Abstract
Abstract 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.
- Authors:
-
- California Inst. of Technology (CalTech), Pasadena, CA (United States)
- Univ. of California, San Diego, CA (United States)
- Publication Date:
- Research Org.:
- Univ. of California, San Diego, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC)
- OSTI Identifier:
- 1344395
- Alternate Identifier(s):
- OSTI ID: 1401120
- Grant/Contract Number:
- SC0009376; DE‐FG02‐13ER16370
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Angewandte Chemie (International Edition)
- Additional Journal Information:
- Journal Name: Angewandte Chemie (International Edition); Journal Volume: 54; Journal Issue: 6; Journal ID: ISSN 1433-7851
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; cyclic alkyl amino carbenes; ethenolysis; olefin metathesis; seed-oil derivatives; terminal olefins
Citation Formats
Marx, Vanessa M., Sullivan, Alexandra H., Melaimi, Mohand, Virgil, Scott C., Keitz, Benjamin K., Weinberger, David S., Bertrand, Guy, and Grubbs, Robert H. Cyclic alkyl amino carbene (CAAC) ruthenium complexes as remarkably active catalysts for ethenolysis. United States: N. p., 2014.
Web. doi:10.1002/anie.201410797.
Marx, Vanessa M., Sullivan, Alexandra H., Melaimi, Mohand, Virgil, Scott C., Keitz, Benjamin K., Weinberger, David S., Bertrand, Guy, & Grubbs, Robert H. Cyclic alkyl amino carbene (CAAC) ruthenium complexes as remarkably active catalysts for ethenolysis. United States. https://doi.org/10.1002/anie.201410797
Marx, Vanessa M., Sullivan, Alexandra H., Melaimi, Mohand, Virgil, Scott C., Keitz, Benjamin K., Weinberger, David S., Bertrand, Guy, and Grubbs, Robert H. Wed .
"Cyclic alkyl amino carbene (CAAC) ruthenium complexes as remarkably active catalysts for ethenolysis". United States. https://doi.org/10.1002/anie.201410797. https://www.osti.gov/servlets/purl/1344395.
@article{osti_1344395,
title = {Cyclic alkyl amino carbene (CAAC) ruthenium complexes as remarkably active catalysts for ethenolysis},
author = {Marx, Vanessa M. and Sullivan, Alexandra H. and Melaimi, Mohand and Virgil, Scott C. and Keitz, Benjamin K. and Weinberger, David S. and Bertrand, Guy and Grubbs, Robert H.},
abstractNote = {Abstract 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.},
doi = {10.1002/anie.201410797},
journal = {Angewandte Chemie (International Edition)},
number = 6,
volume = 54,
place = {United States},
year = {Wed Dec 17 00:00:00 EST 2014},
month = {Wed Dec 17 00:00:00 EST 2014}
}
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Figure 1: Selected ruthenium metathesis catalysts previously studied for ethenolysis.
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