An (NH4)2S2O8-promoted cross-coupling of thiols/diselenides and sulfoxides for the synthesis of unsymmetrical disulfides/selenosulfides

Ma, Yang-Tong; Lin, Chao; Huang, Xiaobo; Liu, Miaochang; Zhou, Yun‐Bing; Wu, Huayue

doi:10.1039/d2cc01344d

Cited by 11 publications

(9 citation statements)

References 45 publications

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“…Additional references cited within the Supporting Information (Ref. [18][19][20][21][22][23][24][25][26]).…”

Section: Methodsmentioning

confidence: 99%

Sulfoxonium Ylides as Carbene Precursors in Rhodium‐Catalyzed Sommelet‐Hauser Rearrangement for the Synthesis of S/Se‐Containing Compounds

Luo,

Lin,

Hao

et al. 2023

Eur J Org Chem

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Rhodium‐catalyzed Sommelet‐Hauser rearrangement derived from α‐thioesters/α‐selenoesters and sulfoxonium ylides has been developed for the synthesis of various sulfur/selenium‐containing ortho‐substituted aromatic compounds in medium to excellent yields (39 examples; up to 97 %). Sulfoxonium ylides as the safe carbene precursors are firstly used in Sommelet‐Hauser rearrangement reactions, which is superior to traditional diazo compounds. The present reaction has the advantages of mild condition, safety and broad substrate scope, which afford a unique method for the synthesis of sulfur/selenium‐containing compounds with a tertiary carbon center.

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“…Additional references cited within the Supporting Information (Ref. [18][19][20][21][22][23][24][25][26]).…”

Section: Methodsmentioning

confidence: 99%

Sulfoxonium Ylides as Carbene Precursors in Rhodium‐Catalyzed Sommelet‐Hauser Rearrangement for the Synthesis of S/Se‐Containing Compounds

Luo,

Lin,

Hao

et al. 2023

Eur J Org Chem

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“…Notably, the desired product was also obtained using an arylthiol, although the reaction yield was low ( 3ac , 10%, NMR yield: 78%). The reduced yield in this case was attributed to the inherent instability of the selenosulfide structure containing the arylthio group . The compound underwent decomposition during column chromatography.…”

mentioning

confidence: 95%

“…The reduced yield in this case was attributed to the inherent instability of the selenosulfide structure containing the arylthio group. 12 The compound underwent decomposition during column chromatography. Moreover, the reaction exhibited tolerance toward acyl or ester group-substituted diazonium salts (3ad: 65%, 3ae: 47%).…”

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confidence: 99%

“…Other attempts involving diselenides or selenocyanates as starting compounds have also been reported (Schemes , I, B). These methods use samarium diiodide, a persulfate/base combination, and trifluoromethanesulfenamide as reagents . Recently, Liu and Zhou developed a robust cross-coupling reaction using ammonium persulfate .…”

mentioning

confidence: 99%

“…These methods use samarium diiodide, a persulfate/base combination, and trifluoromethanesulfenamide as reagents . Recently, Liu and Zhou developed a robust cross-coupling reaction using ammonium persulfate . This innovative method allows for the efficient synthesis of selenosulfides.…”

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confidence: 99%

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Base-Catalyzed One-Pot Synthesis of Selenosulfides: A Base Basicity-Controlled Approach

Lee,

Sim,

Lee

2023

J. Org. Chem.

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We developed a novel and efficient sequential one-pot synthesis of selenosulfides via a base-catalyzed methodology utilizing readily available starting compounds, under mild reaction conditions. This method eliminated the need for excess oxidants or additives and simplified the synthesis procedure. Furthermore, organic amine bases served as exceptional catalysts for synthesizing the target products. The performance of a catalytic system depends on the basicity of the bases. The selection of suitable bases, based on their pK aH values, is crucial for the selective synthesis of selenosulfides without the formation of byproducts. This method provides a direct route for the preparation of selenosulfides, which are important scaffolds in organic chemistry.

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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.

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An (NH₄)₂S₂O₈-promoted cross-coupling of thiols/diselenides and sulfoxides for the synthesis of unsymmetrical disulfides/selenosulfides

Abstract: (NH4)2S2O8-Promoted cross-coupling of thiols/diselenides and sulfoxides to construct unsymmetrical disulﬁdes/selenosulfides is disclosed. Control experiments demonstrate that (NH4)2S2O8 acts as an acid and an oxidant while both ionic and radical routes...

Cited by 11 publications

References 45 publications

Sulfoxonium Ylides as Carbene Precursors in Rhodium‐Catalyzed Sommelet‐Hauser Rearrangement for the Synthesis of S/Se‐Containing Compounds

Sulfoxonium Ylides as Carbene Precursors in Rhodium‐Catalyzed Sommelet‐Hauser Rearrangement for the Synthesis of S/Se‐Containing Compounds

Base-Catalyzed One-Pot Synthesis of Selenosulfides: A Base Basicity-Controlled Approach

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

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