Keitz, Benjamin K. and Endo, Koji and Patel, Paresma R. and Herbert, Myles B. and Grubbs, Robert H. (2012) Improved Ruthenium Catalysts for Z-Selective Olefin Metathesis. Journal of the American Chemical Society, 134 (1). pp. 693-699. ISSN 0002-7863 http://resolver.caltech.edu/CaltechAUTHORS:20120403-082650298
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Abstract
Several new C–H-activated ruthenium catalysts for Z-selective olefin metathesis have been synthesized. Both the carboxylate ligand and the aryl group of the N-heterocyclic carbene have been altered and the resulting catalysts evaluated using a range of metathesis reactions. Substitution of bidentate with monodentate X-type ligands led to a severe attenuation of metathesis activity and selectivity, while minor differences were observed between bidentate ligands within the same family (e.g., carboxylates). The use of nitrato-type ligands in place of carboxylates afforded a significant improvement in metathesis activity and selectivity. With these catalysts, turnover numbers approaching 1000 were possible for a variety of cross-metathesis reactions, including the synthesis of industrially relevant products.
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| Additional Information: | © 2011 American Chemical Society. Received: October 31, 2011. Publication Date (Web): November 19, 2011. Lawrence Henling and Dr. Michael Day are acknowledged for X-ray crystallographic analysis. Dr. David VanderVelde is thanked for assistance with NMR experimentation and analysis. This work was financially supported by the NIH (NIH 5R01GM031332-27), the NSF (CHE-1048404), Mitsui Chemicals, Inc. (K.E.), and the NDSEG (fellowship to B.K.K.). Instrumentation on which this work was carried out were supported by the NSF (X-ray diffractometer, CHE- 0639094) and the NIH (NMR spectrometer, RR027690). Materia, Inc. is thanked for its donation of metathesis catalysts. Author Contributions ‡These authors contributed equally | ||||||||||||||||
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| Record Number: | CaltechAUTHORS:20120403-082650298 | ||||||||||||||||
| Persistent URL: | http://resolver.caltech.edu/CaltechAUTHORS:20120403-082650298 | ||||||||||||||||
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| Official Citation: | Improved Ruthenium Catalysts for Z-Selective Olefin Metathesis Benjamin K. Keitz, Koji Endo, Paresma R. Patel, Myles B. Herbert, and Robert H. Grubbs Journal of the American Chemical Society 2012 134 (1), 693-699 | ||||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||||
| ID Code: | 29947 | ||||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||||
| Deposited By: | Ruth Sustaita | ||||||||||||||||
| Deposited On: | 03 Apr 2012 15:45 | ||||||||||||||||
| Last Modified: | 26 Dec 2012 15:01 |
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