Metal-free and atom-efficient protocol for diarylation of selenocyanate by diaryliodonium salts

Radzhabov, Amirbek D.; Soldatova, Natalia S.; Ivanov, Denis; Yusubov, Mekhman S.; Kukushkin, Vadim Yu.; Postnikov, Pavel

doi:10.1039/d3ob00833a

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob00833a

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Metal-free and atom-efficient protocol for diarylation of selenocyanate by diaryliodonium salts

Amirbek D. Radzhabov

Natalia S. Soldatova

Denis Ivanov

et al.

Abstract: The rational search for the efficient protocols for atom-efficient arylation utilizing iodonium salts is the genuine need for the sustainability and green chemistry. We developed a novel approach toward metal-free...

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Cited by 6 publications

References 56 publications

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Synthesis of Selenium Derivatives using Organic Selenocyanates as Masked Selenols: Chemical Reduction with Rongalite as a Simpler Tool to give Nucleophilic Selenides

Castro‐Godoy,

Heredia,

Bouchet

et al. 2024

ChemPlusChem

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The chemical reduction within a family of organic selenocyanates, as masked selenols, using reducing agents, such as Rongalite, sodium dithionite, and sodium thiosulfate is investigated. Using Rongalite, the corresponding diselenides were obtained quantitatively and selectively in very good to excellent yields (51‐100%) starting from alkyl, aryl, and benzyl selenocyanates. The scope of the reaction is unaffected by the electronic nature of the substituents. Furthermore, the reducing agent, Rongalite, is compatible with hydrolysable and reducing‐sensitive functional groups. Additionally, a simple methodology employing the in‐situ generated benzyl selenolate anion (PhCH2Se‾) to promote aliphatic nucleophilic substitution, epoxide ring opening, and Michael addition reactions has been developed; thus extending the structural diversity of the synthesized selenium derivatives.

show abstract

Synthesis of Selenium Derivatives using Organic Selenocyanates as Masked Selenols: Chemical Reduction with Rongalite as a Simpler Tool to give Nucleophilic Selenides

Castro‐Godoy,

Heredia,

Bouchet

et al. 2024

ChemPlusChem

View full text Add to dashboard Cite

show abstract

Transition metal-free C(sp³)–H selenation of β-ketosulfones

Abdukerem,

Chen,

Mao

et al. 2024

Org. Biomol. Chem.

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Scientific School of Academician V.Yu. Kukushkin at St. Petersburg University (A Review)

Kinzhalov

2024

Russ J Gen Chem

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Metal-free and atom-efficient protocol for diarylation of selenocyanate by diaryliodonium salts

Abstract: The rational search for the efficient protocols for atom-efficient arylation utilizing iodonium salts is the genuine need for the sustainability and green chemistry. We developed a novel approach toward metal-free...

Cited by 6 publications

References 56 publications

Synthesis of Selenium Derivatives using Organic Selenocyanates as Masked Selenols: Chemical Reduction with Rongalite as a Simpler Tool to give Nucleophilic Selenides

Synthesis of Selenium Derivatives using Organic Selenocyanates as Masked Selenols: Chemical Reduction with Rongalite as a Simpler Tool to give Nucleophilic Selenides

Transition metal-free C(sp³)–H selenation of β-ketosulfones

Scientific School of Academician V.Yu. Kukushkin at St. Petersburg University (A Review)

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Metal-free and atom-efficient protocol for diarylation of selenocyanate by diaryliodonium salts

Abstract: The rational search for the efficient protocols for atom-efficient arylation utilizing iodonium salts is the genuine need for the sustainability and green chemistry. We developed a novel approach toward metal-free...

Cited by 6 publications

References 56 publications

Synthesis of Selenium Derivatives using Organic Selenocyanates as Masked Selenols: Chemical Reduction with Rongalite as a Simpler Tool to give Nucleophilic Selenides

Synthesis of Selenium Derivatives using Organic Selenocyanates as Masked Selenols: Chemical Reduction with Rongalite as a Simpler Tool to give Nucleophilic Selenides

Transition metal-free C(sp3)–H selenation of β-ketosulfones

Scientific School of Academician V.Yu. Kukushkin at St. Petersburg University (A Review)

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Product

Resources

About

Transition metal-free C(sp³)–H selenation of β-ketosulfones