Efficient and Selective Peracetic Acid Epoxidation Catalyzed by a Robust Manganese Catalyst

Isaac Garcia-Bosch†, Anna Company†, Xavier Fontrodona‡, Xavi Ribas† and Miquel Costas†
Departament de Química, Campus de Montilivi, E-17071 Girona, Catalonia, Spain, and Serveis Tècnics de Recerca, Universitat de Girona, E-17071 Girona, Catalonia, Spain
Org. Lett., 2008, 10 (11), pp 2095–2098
DOI: 10.1021/ol800329m
Publication Date (Web): April 25, 2008
Copyright © 2008 American Chemical Society
, †

Departament de Química.

, ‡

Serveis Tècnics de Recerca.

Abstract

Abstract Image

A manganese catalyst containing a tetradentate ligand derived from triazacyclononane exhibits high catalytic activity in epoxidation reactions using peracetic acid as oxidant. The system exhibits broad substrate scope and requires small (0.1−0.15 mol %) catalyst loading. The catalyst is remarkably selective toward aliphatic cis-olefins. Mechanistic studies point toward an electrophilic oxidant delivering the oxygen atom in a concerted step.

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    History

    • Published In Issue June 05, 2008
    • Article ASAPApril 25, 2008
    • Received: February 13, 2008

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