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Single‐Face/All‐ cis Arene Hydrogenation by a Supported Single‐Site d 0 Organozirconium Catalyst
Author(s) -
Stalzer Madelyn Marie,
Nicholas Christopher P.,
Bhattacharyya Alak,
Motta Alessandro,
Delferro Massimiliano,
Marks Tobin J.
Publication year - 2016
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.201600345
Subject(s) - cyclohexanes , catalysis , chemistry , intramolecular force , alkylation , stereochemistry , organic chemistry
The single‐site supported organozirconium catalyst Cp*ZrBz 2 /ZrS (Cp*=Me 5 C 5 , 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 π‐face interchange.