Salicylaldimine Ruthenium Alkylidene Complexes: Metathesis Catalysts Tuned for Protic Solvents.

Advanced Synthesis & Catalysis
Joseph B BinderRonald T Raines

Abstract

Tuning the electronic and steric environment of olefin metathesis catalysts with specialized ligands can adapt them to broader applications, including metathesis in aqueous solvents. Bidentate salicylaldimine ligands are known to stabilize ruthenium alkylidene complexes, as well as allow ring-closing metathesis in protic media. Here, we report the synthesis and characterization of exceptionally robust olefin metathesis catalysts bearing both bidentate salicylaldimine and N-heterocyclic carbene ligands, including a trimethylammonium-functionalized complex adapted for polar solvents. NMR spectroscopy and X-ray crystallographic analysis confirm the structures of the complexes. Although the N-heterocyclic carbene-salicylaldimine ligand combination limits the activity of these catalysts in nonpolar solvents, this pairing enables efficient ring-closing metathesis of both dienes and enynes in methanol and methanol-water mixtures under air.

References

Jul 6, 2001·Journal of the American Chemical Society·M S SanfordR H Grubbs
Jul 18, 2001·Journal of the American Chemical Society·D M Lynn, R H Grubbs
Oct 25, 2001·The Journal of Organic Chemistry·Shana J. Sturla, Stephen L. Buchwald
Feb 21, 2002·Journal of the American Chemical Society·Christopher W CairoLaura L Kiessling
Jun 28, 2002·Bioorganic & Medicinal Chemistry Letters·Stephen J Connon, Siegfried Blechert
Aug 31, 2002·Angewandte Chemie·Hideaki Wakamatsu, Siegfried Blechert
Dec 12, 2002·Journal of the American Chemical Society·Jason E GestwickiLaura L Kiessling
Aug 14, 2003·Journal of the American Chemical Society·Jennifer A LoveRobert H Grubbs
Dec 4, 2003·Current Opinion in Chemical Biology·Michiel A LeeuwenburghHerman S Overkleeft
Jun 17, 2005·Organic Letters·Cara L JenkinsRonald T Raines
Jul 9, 2005·Angewandte Chemie·K C NicolaouDavid Sarlah
Aug 25, 2005·Journal of the American Chemical Society·Jay C ConradDeryn E Fogg
Dec 28, 2005·Current Topics in Medicinal Chemistry·Pierre Van de WegheJanine Cossy
Dec 28, 2005·Current Topics in Medicinal Chemistry·Pierre Van de Weghe, Jacques Eustache
Dec 28, 2005·Current Topics in Medicinal Chemistry·William H C Martin, Siegfried Blechert
Dec 28, 2005·Current Topics in Medicinal Chemistry·Luigi A Agrofoglio, Steven P Nolan
Dec 28, 2005·Current Topics in Medicinal Chemistry·Joëlle Prunet
Mar 16, 2006·Journal of the American Chemical Society·Soon Hyeok Hong, Robert H Grubbs
Mar 25, 2006·Angewandte Chemie·Laura L KiesslingLaura E Strong

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Citations

Feb 13, 2013·Journal of the American Chemical Society·Giovanni OcchipintiVidar R Jensen
Oct 22, 2008·Current Opinion in Chemical Biology·Joseph B Binder, Ronald T Raines
Oct 1, 2011·Chemistry : a European Journal·Cezary SamojłowiczKarol Grela
Jun 6, 2007·Angewandte Chemie·Jason P Jordan, Robert H Grubbs
Nov 7, 2007·Dalton Transactions : an International Journal of Inorganic Chemistry·Nele LedouxFrancis Verpoort
Feb 1, 2008·Chemistry : a European Journal·Joseph S M Samec, Robert H Grubbs
Nov 5, 2008·Angewandte Chemie·Daniel Burtscher, Karol Grela
Apr 4, 2009·Chembiochem : a European Journal of Chemical Biology·Yuya A LinBenjamin G Davis
Feb 2, 2011·Beilstein Journal of Organic Chemistry·Yuya A Lin, Benjamin G Davis
Jun 13, 2012·Chemistry : a European Journal·Georgios C Vougioukalakis
Dec 15, 2015·Beilstein Journal of Organic Chemistry·Lorenzo PiolaSteven P Nolan
Jul 31, 2012·Chemical Society Reviews·Heriberto Diaz Velazquez, Francis Verpoort
Dec 17, 2009·Chemical Reviews·Georgios C Vougioukalakis, Robert H Grubbs
Apr 24, 2009·Chemical Reviews·Nuno R CandeiasAlexandre F Trindade
Jun 19, 2009·Chemical Reviews·Cezary SamojłowiczKarol Grela
May 6, 2015·Chemical Reviews·Efrat LevinN Gabriel Lemcoff
Jul 17, 2020·Journal of the American Chemical Society·Jeffrey C FosterRachel K O'Reilly
Jan 29, 2008·Journal of the American Chemical Society·Georgios C Vougioukalakis, Robert H Grubbs

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