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Manganese catalysts with molecular recognition functionality for selective alkene epoxidation.

Jonathan F Hull¹, Effiette L O Sauer, Christopher D Incarvito

¹Chemistry Department, Yale University, 225 Prospect Street, New Haven, Connecticut 06511, USA.

Inorganic Chemistry

|December 20, 2008

Summary

A new manganese porphyrin catalyst, C(PMR), enables selective alkene epoxidation through hydrogen bonding. Molecular recognition directs oxidation to olefins, yielding only epoxides and outperforming a manganese terpyridine complex.

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Area of Science:

Catalysis
Organic Chemistry
Materials Science

Background:

Selective alkene epoxidation is crucial in organic synthesis.
Developing catalysts that utilize molecular recognition for enhanced selectivity is an ongoing challenge.
Manganese complexes have shown promise as oxidation catalysts.

Purpose of the Study:

To synthesize and evaluate a new manganese porphyrin catalyst, C(PMR), for selective alkene epoxidation.
To investigate the role of hydrogen bonding and molecular recognition in directing the catalytic reaction.
To compare the performance of C(PMR) with a known manganese terpyridine catalyst, C(TMR).

Main Methods:

Synthesis of the manganese porphyrin catalyst C(PMR).
Epoxidation reactions using various olefin substrates and the C(PMR) catalyst.
Analysis of reaction products to determine selectivity and diastereoselectivity.
Molecular modeling to understand substrate-catalyst interactions.
Comparison of C(PMR) performance with the C(TMR) catalyst.

Main Results:

The C(PMR) catalyst achieved selective epoxidation of alkenes via hydrogen bonding between the substrate's carboxylic acid and the catalyst's Kemp's triacid unit.
For two of three substrates, molecular recognition prevented C-H bond oxidation, exclusively forming epoxide products.
Weak diastereoselectivity was observed, indicating substrate orientation influenced by molecular recognition.
The manganese terpyridine complex C(TMR) demonstrated superior catalytic activity compared to C(PMR).
Molecular modeling supported good substrate/catalyst compatibility for substrate S2 with C(PMR).

Conclusions:

Hydrogen bonding is critical for the selective epoxidation catalyzed by C(PMR).
Molecular recognition plays a key role in directing the catalyst's activity and achieving high selectivity.
While C(PMR) shows promise, C(TMR) remains a more effective catalyst for alkene epoxidation in this study.