Compartmentalization of Incompatible Catalytic Transformations for Tandem Catalysis

In Nature, incompatible catalytic transformations are being carried out simultaneously through compartmentalization that allows for the combination of incompatible catalysts in tandem reactions. Herein, we take the compartmentalization concept to the synthetic realm and present an approach that allo...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-10, Vol.137 (40), p.12984-12989
Main Authors: Lu, Jie, Dimroth, Jonas, Weck, Marcus
Format: Article
Language:English
Subjects:
Catalysis
Catalysts
Chemical reactions
Hydration
Hydrocarbons
INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Micelles
Polymers - chemistry
Proton Magnetic Resonance Spectroscopy
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Summary:In Nature, incompatible catalytic transformations are being carried out simultaneously through compartmentalization that allows for the combination of incompatible catalysts in tandem reactions. Herein, we take the compartmentalization concept to the synthetic realm and present an approach that allows two incompatible transition metal catalyzed transformations to proceed in one pot in tandem. The key is the site isolation of both catalysts through compartmentalization using a core–shell micellar support in an aqueous environment. The support is based on amphiphilic triblock copolymers of poly­(2-oxazoline)­s with orthogonal functional groups on the side chain that can be used to cross-link covalently the micelle and to conjugate two metal catalysts in different domains of the micelle. The micelle core and shell provide different microenvironments for the transformations: Co-catalyzed hydration of an alkyne proceeds in the hydrophobic core, while the Rh-catalyzed asymmetric transfer hydrogenation of the intermediate ketone into a chiral alcohol occurs in the hydrophilic shell.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b07257