Compartmentalized Nanoreactors for One-Pot Redox-Driven Transformations

Qu, Peiyuan; Kuepfert, Michael; Jockusch, Steffen; Weck, Marcus

doi:10.1021/acscatal.8b04667

Title: Compartmentalized Nanoreactors for One-Pot Redox-Driven Transformations

Journal Article · Thu Feb 21 00:00:00 EST 2019 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.8b04667· OSTI ID:1657171

Qu, Peiyuan ^[1]; Kuepfert, Michael ^[1];

^[2];

^[1]

New York University, NY (United States)
Columbia University, New York, NY (United States)

This contribution introduces poly(2-oxazoline)-based shell cross-linked micelles (SCMs) as nanoreactors to realize one-pot redox-driven deracemizations of secondary alcohols in aqueous media. TEMPO and Rh-TsDPEN moieties are spatially positioned into the hydro-philic corona and the hydrophobic micelle core, respectively. TEMPO catalyzes the oxidation of racemic secondary alcohols into ketones while Rh-TsDPEN catalyzes the asymmetric transfer hydrogenation (ATH) of these ketones to afford enantioenriched secondary alco-hols. Both catalysts, the Rh-TsDPEN complex and TEMPO are incompatible with each other and the SCMs are designed to provide indispensable catalyst site-isolation. Kinetic studies show that the SCMs enhance the reactivity of the immobilized catalysts, compared to those for the unsupported analogs under the same reaction conditions. In conclusion, our nanoreactors can perform deracemizations on a broad range of secondary alcohol substrates and are reusable in a continuous manner while maintaining high activity.

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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)

Grant/Contract Number:: FG02-03ER15459

OSTI ID:: 1657171

Journal Information:: ACS Catalysis, Vol. 9, Issue 4; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 48 works

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Cross-linked micelle
poly(2-oxazoline)
deracemization
TEMPO oxidation
asymmetric transfer hydrogenation
oxidation reactions
catalysts
redox reaction
oxidation
nanodevices

Title: Compartmentalized Nanoreactors for One-Pot Redox-Driven Transformations

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