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Z-Selective Olefin Metathesis Reactions Promoted by Tungsten Oxo Alkylidene Complexes

Author(s)
Takase, Michael K.; Hoveyda, Amir H.; Peryshkov, Dmitry; Schrock, Richard Royce; Muller, Peter
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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).
Date issued
2011-11
URI
http://hdl.handle.net/1721.1/82554
Department
Massachusetts Institute of Technology. Department of Chemistry
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
ISSN
0002-7863
1520-5126

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