Single-Face/All-cis Arene Hydrogenation by a Supported Single-Site d0 Organozirconium Catalyst

Madelyn Marie Stalzer, Christopher P. Nicholas, Alak Bhattacharyya, Alessandro Motta, Massimiliano Delferro, Tobin J. Marks

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The single-site supported organozirconium catalyst Cp∗ZrBz2/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 H2 delivery to a single catalyst-bound arene face, versus any competing intramolecular arene π-face interchange. Stereocontrol is on: A single-site supported organozirconium catalyst exhibits unprecedented all-cis stereo/face-selective hydrogenation of substituted alkylarenes under mild reaction conditions. The resulting stereopure cycloalkanes offer new building blocks for value-added fine chemicals.

Original languageEnglish
Pages (from-to)5263-5267
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number17
DOIs
Publication statusPublished - Apr 18 2016

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Keywords

  • DFT calculations
  • Organozirconium catalyst
  • Stereoselective hydrogenation
  • Sulfated oxides
  • Supported catalysts

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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