Different Bonds Cleavage of Arenesulfonates: Access to Diverse Aryl Ethers

Fang, Yongsheng; Li, Wenhui; Jun, Lin; Li, Xing

doi:10.6023/a21050211

Cited by 4 publications

(1 citation statement)

References 55 publications

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“…[24] Methylation can also modify the solubility of drug molecules and improve the off-target selective as well. [25] The popular alkylation reagents, including alkyl halides, [26] dimethyl sulfates, [27] alkyl sulfonates [28,29] have been restricted for their environmental toxicity, potential danger to health and/or genotoxicity. [30][31][32][33][34] Safe and effective reagents are still in limited supply.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound‐Mediated Monodesulfonation of Polyphenol Sulfonate and One‐Pot Generation of Alkyl Aryl Ether under Solvent‐Free Conditions

et al. 2023

ChemistrySelect

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An effective approach for monodesulfonation of polyphenol sulfonate under ultrasonic irradiation was reported. Series of substituted ortho‐, meta‐ or para‐hydroxylphenol sulfonates or 5‐hydroxy‐1,3‐phenylene bis(4‐methylbenzenesulfonate) were obtained specifically in the presence of sodium hydroxide in acetonitrile. With treatment of potassium carbonate in alcohol, alkyloxylphenol sulfonates was provided via one‐pot monodesulfanation followed by alkylation under ultrasonicated solvent‐free conditions. The alcohol had been regarded as green alkylation reagent. The results of the exploration of the scalability of monodesulfonation and one‐pot monodesulfonation‐alkylation of resorcinol bissulfonate indicated that such modes had the potential application value in scale production.

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Section: Introductionmentioning

confidence: 99%

Ultrasound‐Mediated Monodesulfonation of Polyphenol Sulfonate and One‐Pot Generation of Alkyl Aryl Ether under Solvent‐Free Conditions

et al. 2023

ChemistrySelect

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Electrochemical Sulfonylation of Indoles with Inorganic Sulfites and Alcohols: Direct Synthesis of Indole Sulfonic Esters

Sun,

Xi,

Wei

et al. 2024

J. Org. Chem.

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A direct electrochemical sulfonylation between indoles, inorganic sulfites, and alcohols was developed, in which various indoyl sulfonate esters were prepared efficiently. In this transformation, the easy-handle and cost-effective inorganic sulfite was disclosed to engage in a Csp 2 −H sulfonylation as the SO 2 source in an undivided electrolysis cell under mild conditions. In addition, the unexpected paired electrosynthesis has been achieved, owing to the dual role of inorganic sulfites, and led to a sulfonylation/reduction sequence to rapidly deliver hydroxyl substituted indole sulfonate esters.

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Substrate-Controlled Electrochemical Reaction of 2-Alkynylbenzamides, Inorganic Sulfites, and Alcohols

Wang,

Feng,

Han

et al. 2024

J. Org. Chem.

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Isoindolones constitute a dominant structural class in synthetic and medicinal chemistry. In this research, an electrochemical reaction involving 2-alkynylbenzamides, inorganic sulfites, and alcohols was first established to provide sulfonyl ester-substituted 3-hydroxyisoindolinone derivatives in moderate to good yields with excellent functional group tolerance. When bulky aryl-substituted 2-alkynylbenzamides are utilized as substrates, sulfonyl ester-substituted 3-alkylideneisoindolinones can be selectively generated with good chemoselectivity. Alkoxysulfonyl radicals derived from the anodic oxidation of inorganic sulfite with alcohols are involved in this transformation.

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Different Bonds Cleavage of Arenesulfonates: Access to Diverse Aryl Ethers

Cited by 4 publications

References 55 publications

Ultrasound‐Mediated Monodesulfonation of Polyphenol Sulfonate and One‐Pot Generation of Alkyl Aryl Ether under Solvent‐Free Conditions

Ultrasound‐Mediated Monodesulfonation of Polyphenol Sulfonate and One‐Pot Generation of Alkyl Aryl Ether under Solvent‐Free Conditions

Electrochemical Sulfonylation of Indoles with Inorganic Sulfites and Alcohols: Direct Synthesis of Indole Sulfonic Esters

Substrate-Controlled Electrochemical Reaction of 2-Alkynylbenzamides, Inorganic Sulfites, and Alcohols

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