Modular approach for the development of supported, monofunctionalized, salen catalysts

Michael Holbach, Marcus Weck

Research output: Contribution to journalArticle

Abstract

We report a modular approach toward polymer-supported, metalated, salen catalysts. This strategy is based on the synthesis of monofunctionalized Mn- and Co-salen complexes attached to a norbornene monomer via a stable phenylene-acetylene linker. The resulting functionalized monomers can be polymerized in a controlled fashion using ring-opening metathesis polymerization. This polymerization method allows for the synthesis of copolymers, resulting in an unprecedented control over the catalyst density and catalytic-site isolation. The obtained polymeric manganese and cobalt complexes were successfully used as supported catalysts for the asymmetric epoxidation of olefins and the hydrolytic kinetic resolution of epoxides. All polymeric catalysts showed outstanding catalytic activities and selectivities comparable to the original catalysts reported by Jacobsen. Moreover, the copolymer-supported catalysts are more active and selective than their homopolymer analogues, providing further proof that catalyst density and site isolation are key toward highly active and selective supported salen catalysts.

Original languageEnglish (US)
Pages (from-to)1825-1836
Number of pages12
JournalJournal of Organic Chemistry
Volume71
Issue number5
DOIs
StatePublished - Mar 5 2006

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Catalysts
Catalyst supports
Copolymers
Monomers
Acetylene
Epoxidation
Catalyst selectivity
Epoxy Compounds
Ring opening polymerization
Alkenes
Manganese
Cobalt
Homopolymerization
Catalyst activity
Polymers
Polymerization
disalicylaldehyde ethylenediamine
Kinetics

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Modular approach for the development of supported, monofunctionalized, salen catalysts. / Holbach, Michael; Weck, Marcus.

In: Journal of Organic Chemistry, Vol. 71, No. 5, 05.03.2006, p. 1825-1836.

Research output: Contribution to journalArticle

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