Jump to main content
Jump to site search

Issue 10, 2013
Previous Article Next Article

Molecularly enlarged S,S-BnTsDPEN ligands for iron-catalyzed asymmetric olefin epoxidation reactions using hydrogen peroxide

Author affiliations

Abstract

A convenient approach for the anchoring of S,S-BnTsDPEN ligands (S,S-N-tosyl-1,2-diphenylethylenediamine) to branched carbosilane scaffolds was investigated. It is based on a high-yielding reductive amination reaction between commercially available S,S-TsDPEN and readily accessible carbosilanes furnished with benzaldehyde terminal fragments. These molecularly enlarged ligands, bearing four S,S-BnTsDPEN units, and their simplified monomeric and “dimeric” analogues were evaluated in iron(III)-catalyzed asymmetric trans-stilbene epoxidation reactions using hydrogen peroxide as an environmentally benign oxidant. The catalytic investigations showed a large degree of variation in the activity and stereoselectivity of the series of DPEN catalysts. In combination with ESI-MS investigations, these data revealed an important role of the ligand orientation in determining the overall activity of the catalyst system. Accordingly, a suitable design of the molecularly enlarged ligands resulted in fully retained activity and selectivity in catalysis. Finally, a number of strategies for the recovery and reuse of the best performing carbosilane-tethered DPEN ligands were explored.

Graphical abstract: Molecularly enlarged S,S-BnTsDPEN ligands for iron-catalyzed asymmetric olefin epoxidation reactions using hydrogen peroxide

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 08 Jul 2013, accepted on 30 Jul 2013 and first published on 31 Jul 2013


Article type: Paper
DOI: 10.1039/C3CY00484H
Citation: Catal. Sci. Technol., 2013,3, 2810-2818
  •   Request permissions

    Molecularly enlarged S,S-BnTsDPEN ligands for iron-catalyzed asymmetric olefin epoxidation reactions using hydrogen peroxide

    V. A. Yazerski, A. Orue, T. Evers, H. Kleijn and R. J. M. Klein Gebbink, Catal. Sci. Technol., 2013, 3, 2810
    DOI: 10.1039/C3CY00484H

Search articles by author