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Tandem Catalysis: The Sequential Mediation of Olefin Metathesis, Hydrogenation, and Hydrogen Transfer with Single-Component Ru Complexes

Louie, Janis and Bielawski, Christopher W. and Grubbs, Robert H. (2001) Tandem Catalysis: The Sequential Mediation of Olefin Metathesis, Hydrogenation, and Hydrogen Transfer with Single-Component Ru Complexes. Journal of the American Chemical Society, 123 (45). pp. 11312-11313. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170411-104617663

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Abstract

Organometallic catalysts are traditionally designed and optimized to mediate a single reaction. However, the increasing demand for expedient and efficient synthetic processes requires the development of organometallic reagents that are capable of catalyzing multiple, mechanistically distinct reactions directly or by simple modification. While the Ru complex (PCy_3)_2Cl_2Ru= CHPh (1) has found extensive use in olefin metathesis, it was also recently shown to be an effective precatalyst for mediating radical additions and hydrogenation reactions. We recently demonstrated all three reactions could be performed in tandem to afford well-defined block copolymers. Herein, we report that complex 1, or its more active derivative 2, is also useful in mediating a variety of other catalytic hydrogenation reactions that include regiospecific ketone and olefin reductions, transfer hydrogenations of ketones, and dehydrogenative oxidations of alcohols. In addition, we demonstrate a variety of “one-pot” tandem metathesis-hydrogenation procedures for the rapid construction of small molecules, including (R)-(-)-Muscone.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja016431eDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja016431ePublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja016431ePublisherSupporting Information
ORCID:
AuthorORCID
Bielawski, Christopher W.0000-0002-0520-1982
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2001 American Chemical Society. Received June 15, 2001; Revised Manuscript Received September 26, 2001; Publication Date (Web): October 17, 2001. The support of the National Institute of Health (NIH) is acknowledged. J.L. is grateful to the NIH for a postdoctoral fellowship. C.B. is grateful to the ACS Division of Organic Chemistry (sponsored by Rohm and Haas) and the National Science Foundation for fellowship support.
Funders:
Funding AgencyGrant Number
NIH Postdoctoral FellowshipUNSPECIFIED
American Chemical Society Division of Organic ChemistryUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
Issue or Number:45
Record Number:CaltechAUTHORS:20170411-104617663
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170411-104617663
Official Citation:Tandem Catalysis:  The Sequential Mediation of Olefin Metathesis, Hydrogenation, and Hydrogen Transfer with Single-Component Ru Complexes Janis Louie, Christopher W. Bielawski, and Robert H. Grubbs Journal of the American Chemical Society 2001 123 (45), 11312-11313 DOI: 10.1021/ja016431e
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76509
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:11 Apr 2017 17:59
Last Modified:03 Oct 2019 17:02

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