An electrochemical method for deborylative selenylation of arylboronic acids under metal- and oxidant-free conditions

Fu, Zhengjiang; Yin, Jian Dong; He, Dongdong; Yi, Xuezheng; Guo, Shengmei; Cai, Hu

doi:10.1039/d1gc02962b

Cited by 20 publications

(16 citation statements)

References 38 publications

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“…Based on the above radical-trapping experiments, CV results, and literature reports, − a plausible mechanism for the electrochemical sulfonylation of organoboronic acids is proposed in Scheme . Initially, sodium p -toluenesulfinate ( 1a ) loses one electron at the anode to generate the oxygen-centered radical A which resonates to the more-stable sulfur-centered sulfonyl radical B .…”

Section: Resultsmentioning

confidence: 94%

Catalyst-Free Electrochemical Sulfonylation of Organoboronic Acids

Yao

Xie

et al. 2023

J. Org. Chem.

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A simple and efficient electrochemical sulfonylation of organoboronic acids with sodium arylsulfinate salts has been reported for the first time. A variety of aryl, heteroaryl, and alkenylsulfones were obtained in good to excellent yields via a simple electrochemical sulfonylation of various arylboronic acids, heterocyclic boronic acids, or alkenylboronic acids with sodium arylsulfinate at room temperature in 5 h under the catalyst-free and additive-free conditions. A plausible mechanism has been proposed based on various radical-trapping and CV control experiments.

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Section: Resultsmentioning

confidence: 94%

Catalyst-Free Electrochemical Sulfonylation of Organoboronic Acids

Yao

Xie

et al. 2023

J. Org. Chem.

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“…Arylboronic acids are stable, nontoxic and widely available compounds, which have been broadly applied in sustainable organic synthesis, advanced material discovery and new drug development [7] . Recently, our group has gained considerable knowledge in electrochemical deborylative halogenation, [8a] seleno/thiocyanation [8b] and selenylation [8c] of arylboronic acids under metal‐free conditions (routes a–c, Scheme 1). [8] Although the group of Fuchigami [9a] and Jørgensen [9b] described the protocols for electrochemical synthesis of phenols from organoboronic acids, [9] unfortunately, the use of continuous oxygen flow and the transformations with too long time in divided cells led to inconvenient operation and reduced efficiency.…”

Section: Introductionmentioning

confidence: 99%

An Electrochemical Method for Deborylative Hydroxylation of Arylboronic Acids under Metal‐free Conditions

Fang

et al. 2022

Chemistry An Asian Journal

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An electrochemical method for the synthesis of (poly)phenols via deborylative hydroxylation of arylborons has been well established under metal‐free conditions, whose practicability and advantage has been highlighted by the preparation of drug molecules and preformation of scalable transformation. Mechanistic studies have demonstrated that superoxide anion radical was involved in the conversion followed by the reaction with arylboronic acid substrate.

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“…This cyclization sequence offers several improvements because the reactions are carried out under transition-metal-free conditions and the reaction led to the cyclization and introduction of the halogen and the organoselenium group as new functionality in the furan ring. Over the last decade, there has been a significant expansion in the methodologies, which describe the introduction of an organoselenium group in the organic substrate . This functionalization is useful because it allows the construction of new chemical bonds in a highly selective manner to make the final product attractive as a starting material for new organic transformations and biological studies …”

Section: Introductionmentioning

confidence: 99%

Potassium tert-Butoxide-Promoted Tandem Cyclization of Organoselenium Alkynyl Aryl Propargyl Ethers

et al. 2022

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Base-promoted cyclization of 3-organoselenyl-methylene-2-alkynyl aryl propargyl ethers has been developed for the synthesis of 3-butylselanyl-methylene benzofurans, 3-methyl-2-alkynyl-benzofurans, and 4-iodo-benzo[b]furan-fused selenopyrans. Under potassium tert-butoxide as the base and tetrahydrofuran as the solvent, at room temperature, 3-organoselenyl-methylene-2-alkynyl aryl propargyl ethers were converted into 3-butylselanyl-methylene benzofurans via a 5-exo-dig mode. Using the same substrate, changing the solvent to dimethylsulfoxide, 3-methyl-2-alkynyl-benzofurans were selectively obtained in good yields. From 3-butylselanyl-methylene benzofurans, 4-iodo-benzo[b]furan-fused selenopyrans were prepared through a nucleophilic cyclization promoted by molecular iodine. The optimization of the reaction conditions showed that the solvents governed the regioselectivity of this cyclization and the initial formation of the dimsyl anion by the reaction of dimethylsulfoxide with potassium tert-butoxide was crucial for the 3-methyl-2-alkynyl-benzofuran preparation. We also proposed the mechanism for the formation of the products, demonstrated that the methodology can be scaled up, and showed the application of the prepared compounds as substrate in further transformations.

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An electrochemical method for deborylative selenylation of arylboronic acids under metal- and oxidant-free conditions

Abstract: An electrochemical deborylative selenylation of arylboronic acids has been developed to produce aryl selenoethers in good yields, whose practicability has been highlighted through the synthesis of bioactive molecules and gram-scale preparation.

Cited by 20 publications

References 38 publications

Catalyst-Free Electrochemical Sulfonylation of Organoboronic Acids

Catalyst-Free Electrochemical Sulfonylation of Organoboronic Acids

An Electrochemical Method for Deborylative Hydroxylation of Arylboronic Acids under Metal‐free Conditions

Potassium tert-Butoxide-Promoted Tandem Cyclization of Organoselenium Alkynyl Aryl Propargyl Ethers

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