Highly Z-Selective Metathesis Homocoupling of Terminal Olefins
Name
Schrock_Highly z-selective.pdf
Size
545.94 KB
Format
Adobe PDF
Checksum (MD5)
7f5882c6c05e322d3edd6cbe8cbe2213
Author(s)
Jiang, Annie J.
Zhao, Yu
Hoveyda, Amir H.
Schrock, Richard Royce
Date Issued
October 2009
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Jiang, Annie J., Yu Zhao, Richard R. Schrock, and Amir H. Hoveyda. “Highly Z-Selective Metathesis Homocoupling of Terminal Olefins.” Journal of the American Chemical Society 131, no. 46 (November 25, 2009): 16630-16631.
Version
Author's final manuscript
Abstract
Mo and W MonoAryloxide-Pyrrolide (MAP) olefin metathesis catalysts can couple terminal olefins to give as high as >98% Z-products in moderate to high yields with as little as 0.2% catalyst. Results are reported for 1-hexene, 1-octene, allylbenzene, allyltrimethylsilane, methyl-10-undecenoate, methyl-9-decenoate, allylB(pinacolate), allylOBenzyl, allylNHTosyl, and allylNHPh. It is proposed that high Z-selectivity is achieved because a large aryloxide only allows metallacyclobutanes to form that contain adjacent cis substituents and because isomerization of Z-product to E-product can be slow in that same steric environment.
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/ja908098t
