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Title: Cyclic alkyl amino carbene (CAAC) ruthenium complexes as remarkably active catalysts for ethenolysis

Abstract

In this paper, 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. Finally, 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:
 [1];  [1];  [2];  [1];  [1];  [2];  [2];  [1]
  1. California Inst. of Technology (CalTech), Pasadena, CA (United States)
  2. 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; 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. doi: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. doi: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 = {In this paper, 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. Finally, 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 = {2014},
month = {12}
}

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Cited by: 39 works
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Works referenced in this record:

Stable Cyclic (Alkyl)(Amino)Carbenes as Rigid or Flexible, Bulky, Electron-Rich Ligands for Transition-Metal Catalysts: A Quaternary Carbon Atom Makes the Difference
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