An efficient and convenient method for the preparation of disulfides from thiols using oxygen as oxidant catalyzed by tert -butyl nitrite

Yi, Shanli; Li, Meichao; Hu, Xinquan; Mo, Weimin; Shen, Zhenlu

doi:10.1016/j.cclet.2016.03.016

Cited by 23 publications

(5 citation statements)

References 60 publications

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“…[ 4‐7 ] The oxidation of thiols to disulfides can not only effectively solve the above problems, but also generate the high value‐added chemicals, displaying important environmental and industrial significance. [ 8‐10 ] Over the past decades, numerous methods have been reported for this process, [ 11‐16 ] among which the aerobic photocatalytic method, economical and eco‐friendly, is considered as the most promising. [ 17‐22 ] Compared with the traditional inorganic semiconductors or noble metal‐containing complex, the organic dyes show enhanced stability, easy modifications and reduced costs, thus garnering much attentions as a photocatalyst.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Immobilizing Triphenylamine with Photoredox Inert Sr²⁺ Forming Sr‐MOF with Controlled Electron Migration for Photocatalytic Oxidation of Thiols to Disulfides

Wang,

Zheng,

Song

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryThe photocatalytic oxidative coupling of thiols is one of the most popular methods to synthesize the disulfides. Triphenylamine and its derivatives (TPAs) are promising for the above reaction, but suffer from the easy polymerization and difficult separation. To overcome these obstacles while controlling the photogenerated electrons transfer directly to target substrates, herein, we constructed one TPA‐based metal‐organic framework (MOF), (Me2NH2)[Sr(TCBPA)]·DMA·3H2O (1), by direct self‐assembly of tris(4′‐carboxybiphenyl)amine (H3TCBPA) and photoredox inert strontium ion (Sr2+). DFT calculations revealed that the valence band maximum (VBM) and the conduction band minimum (CBM) are mainly located on TCBPA3–, successfully inhibiting the undesirable electron migration to metal nodes. Experimental results indicated that 1 displays superior performance than homogeneous H3TCBPA, which may result from the abundant π···π and C—H···π interactions between the well‐arranged TCBPA3– and the build‐in electric field between the anionic framework and the Me2NH2+. This work highlights that immobilizing TPAs into MOFs is one promising approach to designing heterogeneous photocatalysts for the synthesis of disulfides by oxidative coupling of thiols.

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Section: Background and Originality Contentmentioning

confidence: 99%

Immobilizing Triphenylamine with Photoredox Inert Sr²⁺ Forming Sr‐MOF with Controlled Electron Migration for Photocatalytic Oxidation of Thiols to Disulfides

Wang,

Zheng,

Song

et al. 2024

Chin. J. Chem.

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“…remarks.-1,2-Bis(2-chlorophenyl)disulfide, 1,2bis(3-chlorophenyl)disulfide, 1,2-bis(2-methoxyphenyl)disulfide, 1,2-bis(3-methoxyphenyl)disulfide and 1,2-didodecyldisulfane were prepared in our laboratory according to literature procedures. 48 Other chemicals and solvents were purchased from commercial suppliers and used without further purification. Gas chromatography (GC) was performed on an Agilent GC7890A system equipped with a SE-54 capillary column and a flame ionization detector (FID).…”

Section: Generalmentioning

confidence: 99%

Electrochemical Sulfenylation of Indoles with Disulfides Mediated by Potassium Iodide

Chen

Niu

Shen

et al. 2018

J. Electrochem. Soc.

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A novel electrochemical system for sulfenylation of indoles with disulfides to generate 3-sulfenylindoles via C-S bond formation mediated by potassium iodide at a low potential was developed. Iodine was electrogenerated from iodide ions at a graphite anode and showed a high catalytic activity for the electrochemical sulfenylation reactions. A variety of aromatic, heteroaromatic and aliphatic disulfides could react with 2-methlyindole to synthesize the corresponding 3-sulfenylindoles in good to excellent yields. In addition, protected and unprotected indoles with various groups, especially electron-donating groups, also performed well in the sulfenylation reactions. The transformation, which proceeded through the redox of iodine and the generation of intermediate 3-iodoindole, provided an efficient and environmentally benign protocol for the synthesis of 3-sulfenylindoles under mild conditions.

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“…Transition metal catalysts used always contain organic ligands such as Co (II) phthalocyanines [19], Mn(III) Schiff-base complex [20], CoSalen [21], and Fe(Pc) [22]. Meanwhile, organic catalysts like tert-butyl nitrite [23], diisopropylamine [24], and TEMPO [25] suffer from difficulties in oxidizing secondary thiols. Recently, non-metallic inorganic catalysts like SiO 2 -Cl have also been developed, while the tedious preparation process has limited their applications [26].…”

Section: Introductionmentioning

confidence: 99%

Application of Iodine as a Catalyst in Aerobic Oxidations: A Sustainable Approach for Thiol Oxidations

Wang,

Chen,

Qin

et al. 2023

Molecules

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Iodine is a well-known oxidant that is widely used in organic syntheses. Thiol oxidation by stoichiometric iodine is one of the most commonly employed strategies for the synthesis of valuable disulfides. While recent advancements in catalytic aerobic oxidation conditions have eliminated the need for stoichiometric oxidants, concerns persist regarding the use of toxic or expensive catalysts. In this study, we discovered that iodine can be used as a cheap, low-toxicity catalyst in the aerobic oxidation of thiols. In the catalytic cycle, iodine can be regenerated via HI oxidation by O2 at 70 °C in EtOAc. This protocol harnesses sustainable oxygen as the terminal oxidant, enabling the conversion of primary and secondary thiols with remarkable efficiency. Notably, all 26 tested thiols, encompassing various sensitive functional groups, were successfully converted into their corresponding disulfides with yields ranging from >66% to 98% at a catalyst loading of 5 mol%.

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An efficient and convenient method for the preparation of disulfides from thiols using oxygen as oxidant catalyzed by tert -butyl nitrite

Cited by 23 publications

References 60 publications

Immobilizing Triphenylamine with Photoredox Inert Sr²⁺ Forming Sr‐MOF with Controlled Electron Migration for Photocatalytic Oxidation of Thiols to Disulfides

Immobilizing Triphenylamine with Photoredox Inert Sr²⁺ Forming Sr‐MOF with Controlled Electron Migration for Photocatalytic Oxidation of Thiols to Disulfides

Electrochemical Sulfenylation of Indoles with Disulfides Mediated by Potassium Iodide

Application of Iodine as a Catalyst in Aerobic Oxidations: A Sustainable Approach for Thiol Oxidations

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An efficient and convenient method for the preparation of disulfides from thiols using oxygen as oxidant catalyzed by tert -butyl nitrite

Cited by 23 publications

References 60 publications

Immobilizing Triphenylamine with Photoredox Inert Sr2+ Forming Sr‐MOF with Controlled Electron Migration for Photocatalytic Oxidation of Thiols to Disulfides

Immobilizing Triphenylamine with Photoredox Inert Sr2+ Forming Sr‐MOF with Controlled Electron Migration for Photocatalytic Oxidation of Thiols to Disulfides

Electrochemical Sulfenylation of Indoles with Disulfides Mediated by Potassium Iodide

Application of Iodine as a Catalyst in Aerobic Oxidations: A Sustainable Approach for Thiol Oxidations

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Immobilizing Triphenylamine with Photoredox Inert Sr²⁺ Forming Sr‐MOF with Controlled Electron Migration for Photocatalytic Oxidation of Thiols to Disulfides

Immobilizing Triphenylamine with Photoredox Inert Sr²⁺ Forming Sr‐MOF with Controlled Electron Migration for Photocatalytic Oxidation of Thiols to Disulfides