Phosphine-mediated disulfide metathesis in aqueous media

Caraballo, Rémi; Sakulsombat, Morakot; Ramström, Olof

doi:10.1039/c0cc03622f

Cited by 31 publications

(17 citation statements)

References 38 publications

(2 reference statements)

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“…The healing process as such is based on disulfide bond re‐shuffling which can be triggered by mild temperatures, shear forces, reduction reactions, or UV‐irradiation. Nucleophilic reagents such as phosphine and thiol groups can further facilitate disulfide bonds scission. Recent developments have shown that elastomers with healing capabilities at room temperature can be developed by the metathesis of disulfide bonds in the absence of catalyst using aromatic disulfides .…”

Section: Introductionmentioning

confidence: 99%

Healable dual organic–inorganic crosslinked sol–gel based polymers: Crosslinking density and tetrasulfide content effect

AbdolahZadeh

Esteves

Zwaag

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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In this article, the first generation of healable solgel based polymers is reported. A dual organic-inorganic crosslinked network is developed containing non-reversible crosslinks and reversible (tetrasulfide) groups. The designed polymer architecture allows thermally induced mesoscale flow leading to damage closure followed by interfacial strength restoration due to reformation of the reversible groups. While the reversible bonds are responsible for the flow and the interface restoration, the irreversible crosslinks control the required mechanical integrity during the healing process. The temperature dependent gap closure kinetics is strongly affected by the crosslinking density and tetrasulfide content. Raman spectroscopy is used to explain the gap closure kinetics in air and dry nitrogen.

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Section: Introductionmentioning

confidence: 99%

Healable dual organic–inorganic crosslinked sol–gel based polymers: Crosslinking density and tetrasulfide content effect

AbdolahZadeh

Esteves

Zwaag

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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“…[14] As ac onsequence,e ach network is interconnected to and interdependentwith another network. Althoughd ynamic disulfide bonds are normally activated under basic conditions, [12d] they can also be elicited in the presence of phosphine- [15] or NHC-based [16] catalysts as well as under ultrasound, [17] grinding [18] and photoirradiation. [19] The photochemical exchange of dithioacetals has not been explored,h owever the photoactivation of their CÀSb ond has been exploited for addition of dithioacetals to alkenes [20] and for deprotection of dithioacetals.…”

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confidence: 99%

Rewiring Chemical Networks Based on Dynamic Dithioacetal and Disulfide Bonds

Orrillo

La–Venia

Escalante

et al. 2018

Chemistry A European J

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The control of the connectivity between nodes of synthetic networks is still largely unexplored. To address this point we take advantage of a simple dynamic chemical system with two exchange levels that are mutually connected and can be activated simultaneously or sequentially. Dithioacetals and disulfides can be exchanged simultaneously under UV light in the presence of a sensitizer. Crossover reactions between both exchange processes produce a fully connected chemical network. On the other hand, the use of acid, base or UV light connects different nodes allowing network rewiring.

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“…[6,12] The readily exchangeable-S ÀS-linkage [13] can be utilized in metathesis reactions to rapidlya ccess diversel ibraries of heterodimeric analoguesf rom as mall number of disulfide building blocks. [8,14] Several methods have been recentlyd eveloped to facilitate the disulfide metathesis reactions using phosphine catalysts [15] or mechano- [9a, 16] and photochemicalp rocesses. [17] However,i t is still an ongoing challenge to address the limitations in substrate scope,e quilibration time and the precision of these methods.…”

mentioning

confidence: 99%

NHC‐Catalyzed Metathesis and Phosphorylation Reactions of Disulfides: Development and Mechanistic Insights

Crocker

Hussein

et al. 2017

Chemistry A European J

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The development of efficient methods for the metathesis and phosphorylation reactions of disulfide compounds is of widespread interest due to their important synthetic utility in polymer, biological, medicinal and agricultural chemistry. Herein, we demonstrate the use of N-heterocyclic carbenes (NHCs) as versatile organocatalysts to promote these challenging reactions under mild conditions. This metal- and oxidant-free protocol is operationally simple with very short reaction times. The interplay between the nucleophilicity and basicity of NHCs in these reactions were also elucidated by NMR studies and high-level ab initio calculations.

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Phosphine-mediated disulfide metathesis in aqueous media

Abstract: Dynamic carbohydrate systems have been efficiently generated through phosphine-mediated disulfide metathesis in aqueous media. The protein compatibility and binding features of the dynamic systems were demonstrated in situ using (1)H STD NMR.

Cited by 31 publications

References 38 publications

Healable dual organic–inorganic crosslinked sol–gel based polymers: Crosslinking density and tetrasulfide content effect

Healable dual organic–inorganic crosslinked sol–gel based polymers: Crosslinking density and tetrasulfide content effect

Rewiring Chemical Networks Based on Dynamic Dithioacetal and Disulfide Bonds

NHC‐Catalyzed Metathesis and Phosphorylation Reactions of Disulfides: Development and Mechanistic Insights

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