Z-Selective Olefin Metathesis Reactions Promoted by Tungsten Oxo Alkylidene Complexes
Name
Scrock_Z-selective olefin metathesis.pdf
Size
627.59 KB
Format
Adobe PDF
Checksum (MD5)
1da34f292eb995092721a45b683eef1f
Author(s)
Takase, Michael K.
Hoveyda, Amir H.
Peryshkov, Dmitry
Schrock, Richard Royce
Muller, Peter
Date Issued
November 2011
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Peryshkov, Dmitry V., Richard R. Schrock, Michael K. Takase, Peter Muller, and Amir H. Hoveyda. “Z-Selective Olefin Metathesis Reactions Promoted by Tungsten Oxo Alkylidene Complexes.” Journal of the American Chemical Society 133, no. 51 (December 28, 2011): 20754-20757.
Version
Author's final manuscript
Abstract
Addition of LiOHMT (OHMT = O-2,6-dimesitylphenoxide) to W(O)(CH-t-Bu)(PMe[subscript 2]Ph)[subscript 2]Cl[subscript 2] led to WO(CH-t-Bu)Cl(OHMT)(PMe[subscript 2]Ph) (4). Subsequent addition of Li(2,5-Me[subscript 2]C[subscript 4]H[subscript 2]N) to 4 yielded yellow W(O)(CH-t-Bu)(OHMT)(Me[subscript 2]Pyr)(PMe[subscript 2]Ph) (5). Compound 5 is a highly effective catalyst for the Z-selective coupling of selected terminal olefins (at 0.2% loading) to give product in >75% yield with >99% Z configuration. Addition of 2 equiv of B(C[subscript 6]F[subscript 5])[subscript 3] to 5 afforded a catalyst activated at the oxo ligand by B(C[subscript 6]F[subscript 5])[subscript 3]. 5·B(C[subscript 6]F[subscript 5])[subscript 3] is a highly active catalyst that produces thermodynamic products (~20% Z).
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1021/ja210349m
