Single-Face/All-cis Arene Hydrogenation by a Supported Single-Site d(0) Organozirconium Catalyst

The single-site supported organozirconium catalyst Cp*ZrBz(2)/ZrS (Cp*=Me5C5, Bz=benzyl, ZrS=sulfated zirconia) catalyzes the single-face/all-cis hydrogenation of a large series of alkylated and fused arene derivatives to the corresponding all-cis-cyclohexanes. Kinetic/mechanistic and DFT analysis a...

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Published inAngewandte Chemie International Edition Vol. 55; no. 17; pp. 5263 - 5267
Main Authors Stalzer, Madelyn Marie, Nicholas, Christopher P., Bhattacharyya, Alak, Motta, Alessandro, Delferro, Massimiliano, Marks, Tobin J.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 18.04.2016
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
NONHEME IRON
AGOSTIC INTERACTIONS
SULFATED ZIRCONIA
METALLOCENIUM ION-PAIRS
supported catalysts
DFT calculations
100-PERCENT ACTIVE-SITES
H BOND ACTIVATION
POLYMERIZATION CATALYSTS
PHASE HYDROGENATION
stereoselective hydrogenation
SURFACE
sulfated oxides
organozirconium catalyst
HETEROGENEOUS CATALYSTS
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Summary:The single-site supported organozirconium catalyst Cp*ZrBz(2)/ZrS (Cp*=Me5C5, Bz=benzyl, ZrS=sulfated zirconia) catalyzes the single-face/all-cis hydrogenation of a large series of alkylated and fused arene derivatives to the corresponding all-cis-cyclohexanes. Kinetic/mechanistic and DFT analysis argue that stereoselection involves rapid, sequential H-2 delivery to a single catalyst-bound arene face, versus any competing intramolecular arene -face interchange.
Bibliography:ObjectType-Article-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201600345