Compartmentalization of Incompatible Catalytic Transformations for Tandem Catalysis

Lu, Jie; Dimroth, Jonas; Weck, Marcus

doi:10.1021/jacs.5b07257

Title: Compartmentalization of Incompatible Catalytic Transformations for Tandem Catalysis

Journal Article · Thu Oct 01 00:00:00 EDT 2015 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.5b07257· OSTI ID:1657176

Lu, Jie ^[1]; Dimroth, Jonas ^[1]; Weck, Marcus ^[1]

New York University, NY (United States)

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.

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Research Organization:: Georgia Institute of Technology, Atlanta, GA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Contributing Organization:: New York University

Grant/Contract Number:: FG02-03ER15459

OSTI ID:: 1657176

Journal Information:: Journal of the American Chemical Society, Vol. 137, Issue 40; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 109 works

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Title: Compartmentalization of Incompatible Catalytic Transformations for Tandem Catalysis

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