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Inexpensive Ruthenium NNS‐Complexes as Efficient Ester Hydrogenation Catalysts with High C=O vs. C=C Selectivities
Author(s) -
Stadler Bernhard M.,
Puylaert Pim,
Diekamp Justus,
van Heck Richard,
Fan Yuting,
Spannenberg Anke,
Hinze Sandra,
de Vries Johannes G.
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701607
Subject(s) - chemistry , ruthenium , catalysis , allylic rearrangement , selectivity , amine gas treating , alcohol , solvent , noyori asymmetric hydrogenation , organic chemistry , medicinal chemistry
Ru(NNS)(PPh 3 )Cl 2 (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.