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Increased Efficiency in Cross-Metathesis Reactions of Sterically Hindered Olefins

Stewart, Ian C. and Douglas, Christopher J. and Grubbs, Robert H. (2008) Increased Efficiency in Cross-Metathesis Reactions of Sterically Hindered Olefins. Organic Letters, 10 (3). pp. 441-444. ISSN 1523-7060. doi:10.1021/ol702624n.

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Efficiency in olefin cross-metathesis reactions is affected upon reducing the steric bulk of N-heterocyclic carbene ligands of ruthenium-based catalysts. For the formation of disubstituted olefins containing one or more allylic substituents, the catalyst bearing N-tolyl groups is more efficient than the corresponding N-mesityl catalyst. In contrast, the formation of trisubstituted olefins is more efficient using the N-mesityl-containing catalyst. A hypothesis to explain this dichotomy is described.

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Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2008 American Chemical Society. Received 29 October 2007. Published online 5 January 2008. Published in print 1 February 2008. The authors thank the NIH (postdoctoral fellowships to I.C.S. and C.J.D. and Grant 5RO1GM-31332 to R.H.G.), Dr. Patricio Romero (Caltech) for helpful discussions, and Materia Inc. for their generous donation of catalysts used in these studies.
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NIH Postdoctoral FellowshipUNSPECIFIED
Issue or Number:3
Record Number:CaltechAUTHORS:20170426-141708843
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Official Citation:Increased Efficiency in Cross-Metathesis Reactions of Sterically Hindered Olefins Ian C. Stewart, Christopher J. Douglas, and Robert H. Grubbs Organic Letters 2008 10 (3), 441-444 DOI: 10.1021/ol702624n
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76957
Deposited By: Ruth Sustaita
Deposited On:26 Apr 2017 23:06
Last Modified:15 Nov 2021 17:04

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