Premium
Selective Hydrogenation and Hydrodeoxygenation of Aromatic Ketones to Cyclohexane Derivatives Using a Rh@SILP Catalyst
Author(s) -
Moos Gilles,
Emondts Meike,
Bordet Alexis,
Leitner Walter
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201916385
Subject(s) - hydrodeoxygenation , ionic liquid , catalysis , chemistry , cyclohexane , deoxygenation , organic chemistry , reactivity (psychology) , phosphonium , rhodium , selectivity , medicine , alternative medicine , pathology
Rhodium nanoparticles immobilized on an acid‐free triphenylphosphonium‐based supported ionic liquid phase (Rh@SILP(Ph 3 ‐P‐NTf 2 )) enabled the selective hydrogenation and hydrodeoxygenation of aromatic ketones. The flexible molecular approach used to assemble the individual catalyst components (SiO 2 , ionic liquid, nanoparticles) led to outstanding catalytic properties. In particular, intimate contact between the nanoparticles and the phosphonium ionic liquid is required for the deoxygenation reactivity. The Rh@SILP(Ph 3 ‐P‐NTf 2 ) catalyst was active for the hydrodeoxygenation of benzylic ketones under mild conditions, and the product distribution for non‐benzylic ketones was controlled with high selectivity between the hydrogenated (alcohol) and hydrodeoxygenated (alkane) products by adjusting the reaction temperature. The versatile Rh@SILP(Ph 3 ‐P‐NTf 2 ) catalyst opens the way to the production of a wide range of high‐value cyclohexane derivatives by the hydrogenation and/or hydrodeoxygenation of Friedel–Crafts acylation products and lignin‐derived aromatic ketones.