Iodine-enabled organoelectrocatalysis: enantioselective cross dehydrogenative coupling of sulfides and aldehydes

Wang, Zhen; Gausmann, Marcel; Dickoff, Jan-Hendrik; Christmann, Mathias

doi:10.1039/d3gc03828a

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2024

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Cited by 3 publications

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“…Initially, I 2 is formed by the anodic oxidation of the iodide ion. 14 Sulfenyl iodide is then generated via the reaction of I 2 with CD 3 SSO 3 Na. 15 Then, the resulting CD 3 SI undergoes a homolysis step and produces iodine and CD 3 S radicals.…”

Section: Resultsmentioning

confidence: 99%

Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD₃SSO₃Na

Zhao,

Zhou,

Zhang

et al. 2024

Org. Chem. Front.

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Section: Resultsmentioning

confidence: 99%

Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD₃SSO₃Na

Zhao,

Zhou,

Zhang

et al. 2024

Org. Chem. Front.

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Azolopyrimidine‐Based Thioethers: Synthesis via Cross‐Dehydrogenative C−S Coupling and In Silico Evaluation of Anti‐SARS‐CoV‐2 Activity

Akulov,

Silaeva,

Varaksin

et al. 2024

ChemPlusChem

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Azoloazine derivatives are known as promising small molecules that are potentially able to counteract a broad spectrum of RNA viruses including SARS‐CoV‐2. However, a pool of synthetic pathways to provide convenient structural modification of such compounds without de novo construction of the heterocyclic scaffold is rather limited so far. This work proposes an approach to the direct C(sp2)–H functionalization of azolopyrimidine substrates with aromatic thiol residues, mediated by the iodine/persulfate reagent system. The reported herein sulfenylation protocol has afforded a series of previously undescribed azolopyrimidine‐based thioethers obtained in yields of up to 87%. Applicability of the approach to the selenium‐centered synthons has been demonstrated as well. Besides, the in silico study with regard to the achieved cross‐coupling products has suggested the possible affinity to the SARS‐CoV‐2 main protease (Mpro), as follows from the conducted pharmacophore search and the molecular docking experiments. As a result, the developed synthetic transformation is expected to be of utility in the design of novel antiviral agents based on small azaheterocyclic molecules.

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Asymmetric cyclopropanation via an electro-organocatalytic cascade

Krech,

Laktsevich-Iskryk,

Deil

et al. 2024

Chem. Commun.

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Iodine-enabled organoelectrocatalysis: enantioselective cross dehydrogenative coupling of sulfides and aldehydes

Abstract: A method for the direct asymmetric α-sulfenylation of aldehydes with sulfides was developed.

Cited by 3 publications

References 30 publications

Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD₃SSO₃Na

Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD₃SSO₃Na

Azolopyrimidine‐Based Thioethers: Synthesis via Cross‐Dehydrogenative C−S Coupling and In Silico Evaluation of Anti‐SARS‐CoV‐2 Activity

Asymmetric cyclopropanation via an electro-organocatalytic cascade

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Iodine-enabled organoelectrocatalysis: enantioselective cross dehydrogenative coupling of sulfides and aldehydes

Abstract: A method for the direct asymmetric α-sulfenylation of aldehydes with sulfides was developed.

Cited by 3 publications

References 30 publications

Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD3SSO3Na

Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD3SSO3Na

Azolopyrimidine‐Based Thioethers: Synthesis via Cross‐Dehydrogenative C−S Coupling and In Silico Evaluation of Anti‐SARS‐CoV‐2 Activity

Asymmetric cyclopropanation via an electro-organocatalytic cascade

Contact Info

Product

Resources

About

Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD₃SSO₃Na

Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD₃SSO₃Na