Highly Z-selective metathesis homocoupling of terminal olefins.

Journal of the American Chemical Society
Annie J JiangAmir H Hoveyda

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.

References

Apr 7, 2005·Journal of the American Chemical Society·Patricio E Romero, Warren E Piers
Dec 15, 2006·Journal of the American Chemical Society·Anna G Wenzel, Robert H Grubbs
Dec 15, 2006·Journal of the American Chemical Society·A S HockAmir H Hoveyda
Jan 25, 2007·Journal of the American Chemical Society·Patricio E Romero, Warren E Piers
May 25, 2007·Journal of the American Chemical Society·Charles Edwin Webster
Dec 18, 2008·Journal of the American Chemical Society·Smaranda C MarinescuAmir H Hoveyda
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Jun 6, 2009·Journal of the American Chemical Society·Annie J JiangRichard R Schrock
Jul 22, 2009·Journal of the American Chemical Society·Smaranda C MarinescuAmir H Hoveyda

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Citations

Aug 12, 2010·Journal of the American Chemical Society·Johannes HeppekausenAlois Fürstner
Apr 23, 2011·Journal of the American Chemical Society·Renee M ThomasRobert H Grubbs
May 14, 2011·Journal of the American Chemical Society·Koji Endo, Robert H Grubbs
Jun 9, 2011·Journal of the American Chemical Society·Benjamin K KeitzRobert H Grubbs
Jul 2, 2011·Journal of the American Chemical Society·Smaranda C MarinescuAmir H Hoveyda
Oct 18, 2011·Journal of the American Chemical Society·Laura C H GerberMichael K Takase
Nov 22, 2011·Journal of the American Chemical Society·Benjamin K KeitzRobert H Grubbs
Nov 24, 2011·Journal of the American Chemical Society·Dmitry V PeryshkovAmir H Hoveyda
Jun 28, 2012·Journal of the American Chemical Society·Erik M TownsendAmir H Hoveyda
Dec 19, 2012·Journal of the American Chemical Society·Vanessa M MarxRobert H Grubbs
Feb 13, 2013·Journal of the American Chemical Society·Giovanni OcchipintiVidar R Jensen
Jan 16, 2013·Journal of the American Chemical Society·Lauren E RosebrughRobert H Grubbs
Apr 4, 2013·Journal of the American Chemical Society·Hiroshi MiyazakiRobert H Grubbs
Apr 17, 2013·Journal of the American Chemical Society·Elizabeth T KiesewetterAmir H Hoveyda
Aug 6, 2013·Journal of the American Chemical Society·Graham E DobereinerJason D Hackenberg
Oct 1, 2013·Journal of the American Chemical Society·Matthew F CainPeter Müller
Sep 11, 2010·Organic Letters·Robert J Ely, James P Morken
Apr 27, 2011·Chemical Communications : Chem Comm·Alois Fürstner
May 7, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Richard R Schrock
Sep 21, 2013·Science·Alois Fürstner
Feb 3, 2011·Beilstein Journal of Organic Chemistry·Christophe Copéret
Aug 31, 2016·Journal of the American Chemical Society·Alessandro GalloSusannah L Scott
Jan 21, 2017·Journal of the American Chemical Society·Tonia S Ahmed, Robert H Grubbs
Oct 28, 2014·Chemical Science·Sarah M BronnerRobert H Grubbs
Dec 13, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Kotohiro Nomura, Xiaohua Hou
Jun 10, 2017·Angewandte Chemie·T Patrick MontgomeryRobert H Grubbs
May 2, 2018·Chemical Society Reviews·O M OgbaR H Grubbs
Oct 13, 2011·Angewandte Chemie·Konrad LehrAlois Fürstner
Jul 9, 2013·Angewandte Chemie·Jeffrey S Cannon, Robert H Grubbs

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