Compartmentalization of Incompatible Catalytic Transformations for Tandem Catalysis
Abstract
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 crosslink covalently the micelle and to conjugate two metal catalysts in different domains of the micelle. Here, 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.
- Authors:
-
- New York University, NY (United States)
- Publication Date:
- Research Org.:
- Georgia Institute of Technology, Atlanta, GA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- Contributing Org.:
- New York University
- OSTI Identifier:
- 1657176
- Grant/Contract Number:
- FG02-03ER15459
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of the American Chemical Society
- Additional Journal Information:
- Journal Volume: 137; Journal Issue: 40; Journal ID: ISSN 0002-7863
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Catalysts; Hydrocarbons; Chemical reactions; Hydration; Micelles
Citation Formats
Lu, Jie, Dimroth, Jonas, and Weck, Marcus. Compartmentalization of Incompatible Catalytic Transformations for Tandem Catalysis. United States: N. p., 2015.
Web. doi:10.1021/jacs.5b07257.
Lu, Jie, Dimroth, Jonas, & Weck, Marcus. Compartmentalization of Incompatible Catalytic Transformations for Tandem Catalysis. United States. https://doi.org/10.1021/jacs.5b07257
Lu, Jie, Dimroth, Jonas, and Weck, Marcus. Thu .
"Compartmentalization of Incompatible Catalytic Transformations for Tandem Catalysis". United States. https://doi.org/10.1021/jacs.5b07257. https://www.osti.gov/servlets/purl/1657176.
@article{osti_1657176,
title = {Compartmentalization of Incompatible Catalytic Transformations for Tandem Catalysis},
author = {Lu, Jie and Dimroth, Jonas and Weck, Marcus},
abstractNote = {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 crosslink covalently the micelle and to conjugate two metal catalysts in different domains of the micelle. Here, 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.},
doi = {10.1021/jacs.5b07257},
journal = {Journal of the American Chemical Society},
number = 40,
volume = 137,
place = {United States},
year = {Thu Oct 01 00:00:00 EDT 2015},
month = {Thu Oct 01 00:00:00 EDT 2015}
}
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