Compartmentalized Nanoreactors for One-Pot Redox-Driven Transformations

Peiyuan Qu, Michael Kuepfert, Steffen Jockusch, Marcus Weck

Research output: Contribution to journalArticle

Abstract

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 hydrophilic 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 alcohols. 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, in comparison to those for the unsupported analogues under the same reaction conditions. Our nanoreactors can perform deracemizations on a broad range of secondary alcohol substrates and are reusable in a continuous manner while maintaining high activity.

Original languageEnglish (US)
Pages (from-to)2701-2706
Number of pages6
JournalACS Catalysis
Volume9
Issue number4
DOIs
StatePublished - Apr 5 2019

Keywords

  • TEMPO oxidation
  • asymmetric transfer hydrogenation
  • cross-linked micelle
  • deracemization
  • poly(2-oxazoline)

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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