Ammonium-tagged ruthenium-based catalysts for olefin metathesis in aqueous media under ultrasound and microwave irradiation

Gułajski, Łukasz; Tracz, Andrzej; Urbaniak, Katarzyna; Czarnocki, Stefan J.; Bieniek, Michał; Olszewski, Tomasz K.

doi:10.3762/bjoc.15.16

Cited by 12 publications

(12 citation statements)

References 82 publications

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“…A sonochemical ring-closing metathesis (RCM) at room temperature, without surfactants or organic cosolvents, takes place inside the water-insoluble droplets of the diene, leading to carbocycles in almost quantitative yields ( Scheme 15 ). 85 The ring-forming process occurs under neat conditions as well, although accompanied by side products resulting from diene oligomerization. The latter was prevented under the micellar conditions attained with sonication.…”

Section: Sonochemical Reactivity: Convergent and Divergent Pathwaysmentioning

confidence: 99%

Organic Sonochemistry: A Chemist’s Timely Perspective on Mechanisms and Reactivity

2021

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Sonochemistry, the use of sound waves, usually within the ultrasonic range (>20 kHz), to boost or alter chemical properties and reactivity constitutes a long-standing and sustainable technique that has, however, received less attention than other activation protocols despite affordable setups. Even if unnecessary to underline the impact of ultrasound-based strategies in a broad range of chemical and biological applications, there is considerable misunderstanding and pitfalls regarding the interpretation of cavitational effects and the actual role played by the acoustic field. In this Perspective, with an eye on mechanisms in particular, we discuss the potentiality of sonochemistry in synthetic organic chemistry through selected examples of past and recent developments. Such examples illustrate specific controlling effects and working rules. Looking back at the past while looking forward to advancing the field, some essentials of sonochemical activation will be distilled.

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Section: Sonochemical Reactivity: Convergent and Divergent Pathwaysmentioning

confidence: 99%

Organic Sonochemistry: A Chemist’s Timely Perspective on Mechanisms and Reactivity

2021

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“…The majority of biologically interesting structures, such as unprotected peptides and carbohydrates, have therefore been largely incompatible with the reactions. To address this limitation, several strategies to enable olefin metathesis in aqueous media have been proposed, including the use of biphasic systems, immobilized catalysts, nanoreactors and micellar catalysis, artificial metallo‐enzymes, as well as modifications of the catalysts or the reaction conditions to increase the reactivity . Unfortunately, many of these systems are either incompatible with water‐soluble substrates or have a very narrow substrate scope …”

Section: Introductionmentioning

confidence: 99%

Acid‐Assisted Direct Olefin Metathesis of Unprotected Carbohydrates in Water

Timmer

Ramström

2019

Chemistry A European J

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The ability to use unprotectedc arbohydrates in olefin metathesis reactions in aqueous media is demonstrated. By using water-soluble, amine-functionalized Hoveyda-Grubbs catalysts under mildly acidic aqueousc onditions, the self-metathesis of unprotecteda lkene-functionalized a-dmanno-and a-d-galactopyranosides could be achieved through minimization of nonproductive chelation and isomerization. Cross-metathesis with allyl alcoholc ould also be achieved with reasonable selectivity. The presence of small quantities (2.5vol %) of acetic acid increased the formation of the self-metathesis product while significantly reducing the alkenei somerization process. The catalytic activityw as furthermore retained in the presenceo fl arge amounts (0.01 mm)o fp rotein, underlining the potential of this carbon-carbon bond-formingr eactionu nder biological conditions. These results demonstrate the potential of directly using unprotectedc arbohydrates tructures in olefin metathesis reactions under mild conditions compatible with biological systems, and therebye nabling their use in, for example, drug discovery and protein derivatization.Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.

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“…21 We decided to add to the family of catalysts containing Cl − or I − as the counterion new members bearing BF 4 − or PF 6 − as the counterion (Figure 2) and to study their activity. 22,23 Additionally, since it is known that the use of more sterically hindered NHC ligands can have a positive effect on the stability of Ru-based active species in olefin metathesis, 24 we also prepared and tested the more bulky catalysts 41a, 41d, 42a, and 42d (Figure 2). The catalysts with BF 4…”

Section: ■ Effect Of the Counterion And The Steric Bulk Of The Aromat...mentioning

confidence: 99%

“…Solubilities of the Catalysts Bearing a Quaternary Ammonium Tag and Different Counterions in Selected Solvents22,23 …”

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confidence: 99%

Ruthenium-Based Complexes Bearing Quaternary Ammonium Tags as Versatile Catalysts for Olefin Metathesis: From the Discovery to Practical Applications

Olszewski

Bieniek²,

Skowerski³

2020

Org. Process Res. Dev.

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Ammonium-tagged ruthenium-based catalysts for olefin metathesis in aqueous media under ultrasound and microwave irradiation

Cited by 12 publications

References 82 publications

Organic Sonochemistry: A Chemist’s Timely Perspective on Mechanisms and Reactivity

Organic Sonochemistry: A Chemist’s Timely Perspective on Mechanisms and Reactivity

Acid‐Assisted Direct Olefin Metathesis of Unprotected Carbohydrates in Water

Ruthenium-Based Complexes Bearing Quaternary Ammonium Tags as Versatile Catalysts for Olefin Metathesis: From the Discovery to Practical Applications

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