A novel and efficient catalytic epoxidation of olefins and monoterpenes with microencapsulated Lewis base adducts of methyltrioxorhenium

The reactivity of methyltrioxorhenium in the epoxidation of olefins can be tuned by the presence of Lewis bases as ligands of the metal center. Unfortunately, a large excess of ligand is usually required to obtain high yields and selectivities mainly because of the fluxional behaviour that these com...

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Bibliographic Details
Published in:Tetrahedron 2005-01, Vol.61 (5), p.1069-1075
Main Authors: Saladino, Raffaele, Andreoni, Alessia, Neri, Veronica, Crestini, Claudia
Format: Article
Language:English
Subjects:
Hydrogen peroxide
Methyltrioxorhenium
Olefins
Oxidation
Terpenes
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Summary:The reactivity of methyltrioxorhenium in the epoxidation of olefins can be tuned by the presence of Lewis bases as ligands of the metal center. Unfortunately, a large excess of ligand is usually required to obtain high yields and selectivities mainly because of the fluxional behaviour that these compounds show in solution. We describe here the microencapsulation technique that can resolve this problem. Microencapsulated Lewis base adducts of methyltrioxorhenium with nitrogen containing ligands are highly efficient and selective catalysts for the epoxidation of several olefins and monoterpenes with hydrogen peroxide even in the case of the most sensitive substrates. These systems show the advantages of the ligand accelerated catalysis and the benefits of heterogeneous compounds. They can be easily recovered from the reaction mixture and used for more transformations. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.11.065