A One-Pot Tandem Olefin Isomerization/Metathesis-Coupling (ISOMET) Reaction
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Author(s)
Dobereiner, Graham E.
Erdogan, Gulin
Larsen, Casey R.
Grotjahn, Douglas B.
Schrock, Richard Royce
Date Issued
July 2014
Journal
ACS Catalysis
Publisher
American Chemical Society (ACS)
Citation
Dobereiner, Graham E., Gulin Erdogan, Casey R. Larsen, Douglas B. Grotjahn, and Richard R. Schrock. “A One-Pot Tandem Olefin Isomerization/Metathesis-Coupling (ISOMET) Reaction.” ACS Catal. 4, no. 9 (September 5, 2014): 3069–3076. © 2014 American Chemical Society
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Final published version
Abstract
A tandem catalytic reaction has been developed as part of a process to discover tungsten-based olefin metathesis catalysts that have a strong preference for terminal olefins over cis or trans internal isomers in olefin metathesis. This tandem isomerization/terminal olefin metathesis reaction (ISOMET) converts C[subscript n] trans internal olefins into C[subscript 2n–2] cis olefins and ethylene. This reaction is made possible with Ru-based “alkene zipper” catalysts, which selectively isomerize trans olefins to an equilibrium mixture of trans and terminal olefins, plus tungsten-based metathesis catalysts that react relatively selectively with terminal olefins to give Z homocoupled products. The most effective catalysts are W(NAr)(C[subscript 3]H[subscript 6])(pyr)(OHIPT) (Ar = 2,6-diisopropylphenyl; pyr = pyrrolide; OHIPT = O-2,6-(2,4,6-i-Pr[subscript 3]C[subscript 6]H[subscript 2])[subscript 2]C[subscript 6]H[subscript 3]) and various [CpRu(P–N)(MeCN)]X (X[superscript –] = [B(3,5-(CF[subscript 3])[subscript 2]C[subscript 6]H[subscript 3])[subscript 4][superscript –]], PF[subscript 6][superscript –], B(C[subscript 6]F[subscript 5])[subscript 4][superscript –]) isomerization catalysts.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/cs500889x
