Inexpensive Ruthenium NNS‐Complexes as Efficient Ester Hydrogenation Catalysts with High C=O vs. C=C Selectivities

Ru(NNS)(PPh3)Cl2 (NNS=2‐(methylthio)‐N‐(pyridin‐2‐yl‐methyl)ethan‐1‐amine) was employed in the hydrogenation of α,β‐unsaturated esters, reaching selectivities for the allylic alcohol up to 95% in the hydrogenation of iso‐butylcinnamate. In addition, several ester substrates were hydrogenated with ca...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-03, Vol.360 (6), p.1151-1158
Main Authors: Stadler, Bernhard M., Puylaert, Pim, Diekamp, Justus, van Heck, Richard, Fan, Yuting, Spannenberg, Anke, Hinze, Sandra, de Vries, Johannes G.
Format: Article
Language:English
Subjects:
allylic compounds
Bonding strength
Catalysis
Catalysts
chemoselectivity
ester hydrogenation
Esters
Hydrogenation
Ruthenium
S-ligands
Substrates
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Summary:Ru(NNS)(PPh3)Cl2 (NNS=2‐(methylthio)‐N‐(pyridin‐2‐yl‐methyl)ethan‐1‐amine) was employed in the hydrogenation of α,β‐unsaturated esters, reaching selectivities for the allylic alcohol up to 95% in the hydrogenation of iso‐butylcinnamate. In addition, several ester substrates were hydrogenated with catalyst loadings as low as 0.05 mol%. Surprisingly, selectivity of the hydrogenation of the C=O vs the C=C bonds strongly depends on the solvent.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201701607