H2O2/NaHCO3-mediated enantioselective epoxidation of olefins in NTf2-based ionic liquids and under ultrasound

Châtel, Grégory; Goux‐Henry, Catherine; Mirabaud, Anaïs; Rossi, Thomas M.; Kardos, N.; Andrioletti, Bruno; Draye, Micheline

doi:10.1016/j.jcat.2012.04.016

Cited by 41 publications

(34 citation statements)

References 40 publications

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“…To unambiguously prove these mechanisms, a chiral Mn porphyrin complex was used as catalyst: in the classical conditions (a), the racemic mixture of epoxides was obtained while in the conditions (b), the ultrasonic asymmetric catalysis in IL clearly showed that the mechanism involves the metalloporphyrin catalyst route. 56 Thus, the IL/US combination improved the yields and decreased reaction times, but also involved a new reactivity for this epoxidation reaction.…”

Section: Synergetic Effects Observed In Organic Chemistrymentioning

confidence: 99%

Ionic liquids and ultrasound in combination: synergies and challenges

2014

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Ionic liquids, as reaction media, and sonochemistry are two recently developing fields of chemistry that present some similarities. Firstly, they constitute separately unconventional approaches to reaction chemistry that, in many cases, generate improvements in yield, rate and selectivity compared to classical chemistry, or even change the mechanisms or products expected. In addition, both are often associated with green chemistry concepts as a result of their properties and their possible eco-friendly uses. A recent trend has been to combine these two technologies in a range of different applications and the results demonstrate very significant and occasionally surprising synergetic effects. Here we critically review the advantages and limitations of the ionic liquid/ultrasound combination in different applications in chemistry, to understand how, and in which respects, it could become an essential tool of sustainable chemistry in the future. Many practical and theoretical aspects associated with this combination of techniques are not understood or resolved and we discus where fundamental studies might further advance this field.

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Section: Synergetic Effects Observed In Organic Chemistrymentioning

confidence: 99%

Ionic liquids and ultrasound in combination: synergies and challenges

2014

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“…A major strength of this approach is that it allows the direct comparison of different routes towards the same target compound. The EcoScale has found favor as an assessment tool in academic laboratories (13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25) and has been modified for industrial purposes (26). It has also been incorporated into some undergraduate pedagogical laboratory exercises (9,27), although it has not, to our knowledge, been utilized as a formal way to evaluate student learning and understanding of green chemistry.…”

Section: A Catalytic Chemistry Coursementioning

confidence: 99%

The EcoScale as a framework for undergraduate green chemistry teaching and assessment

Dicks

Hent

Koroluk

2018

Green Chemistry Letters and Reviews

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An upper-year undergraduate practical examination is presented that utilizes the EcoScale (a semiquantitative tool) and several established mass metrics to assess student understanding of green chemistry principles. This activity focuses on the straightforward preparation of a benzodiazepine via three different catalytic methods, and the analysis of individual experimental data during laboratory time. Students learn about the structure of the EcoScale, apply it as a simplistic life cycle assessment, and critique it as a scientific model. The examination complements more traditional expository and self-design experiments within a synthetic course where green chemistry and sustainability are central themes. ARTICLE HISTORY

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“…Only a small excess of oxidant versus alkene was necessary for these reactions [175]. It has been also demonstrated that the benign H 2 O 2 /NaHCO 3 oxidative combination can be used for the enantioselective epoxidation of olefins using a chiral manganese porphyrin as a catalyst [176]. This unprecedented result was made possible by the use of an ionic liquid with ultrasound, which leads to the activation of Mn-porphyrin catalysis but the enantioselectivity of the epoxidation was moderate (maximum ee: 40%) [176].…”

Section: Manganese Porphyrinmentioning

confidence: 99%

Metal-catalyzed asymmetric sulfoxidation, epoxidation and hydroxylation by hydrogen peroxide

Srour

Maux

Chevance

et al. 2013

Coordination Chemistry Reviews

156

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International audienceThe development of environmentally benign reactions is an important goal in synthetic organic chemistry and chemical engineering. However, catalytic enantioselective oxidations using transition-metal complexes are limited when the oxidant is hydrogen peroxide. The two main difficulties of using hydrogen peroxide in the presence of transition metal complexes are the homolytic cleavage generating OH radicals and the catalase reaction with formation of dioxygen. The current applications of asymmetric sulfoxidation, epoxidation, dihydroxylation of alkenes and hydroxylation will be herein reported. Use of non-heme systems will be presented. The possibility of asymmetric oxidation catalyzed by metalloporphyrins will also be discussed

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H2O2/NaHCO3-mediated enantioselective epoxidation of olefins in NTf2-based ionic liquids and under ultrasound

Cited by 41 publications

References 40 publications

Ionic liquids and ultrasound in combination: synergies and challenges

Ionic liquids and ultrasound in combination: synergies and challenges

The EcoScale as a framework for undergraduate green chemistry teaching and assessment

Metal-catalyzed asymmetric sulfoxidation, epoxidation and hydroxylation by hydrogen peroxide

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