Recent Progress in Aryl Radical-Mediated Cyclization of Unsaturated Bonds Based on Aryldiazonium Salts

Jiang, Song; Nan, Ning; He, Jinghao; Guo, Jiacheng; Qin, Jing‐Hao; Xie, Yu; Ouyang, Xuan‐Hui; Song, Ren‐Jie

doi:10.6023/cjoc202210013

Cited by 7 publications

(2 citation statements)

References 87 publications

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“…Based on the literature reports, control experiment and CV analysis, − the pathway for the electrochemical arylation of C(sp 2 )–H with aryl tetrafluoroborate diazonium salt are proposed and explained in Scheme . First, the phenyl tetrafluoroborate diazonium salt ( 2a ) is initially reduced at the surface of the cathode to generate the corresponding phenyl diazo radical ( A ).…”

Section: Results and Discussionmentioning

confidence: 99%

Electrochemical C–H Arylation of Quinazolinone with Aryl Tetrafluoroborate Diazonium Salts in Aqueous Solution of Ionic Liquids

Ji,

Zhang,

Zhao

et al. 2023

ACS Sustainable Chem. Eng.

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A process for the electrochemical direct C−H arylation of quinazolinones and aryl tetrafluoroborate diazonium salts with ionic liquid [EMIM]BF 4 (1-ethyl-3-methylimidazolium tetrafluoroborate):H 2 O (2:1) as electrolyte was developed for the synthesis of 2-arylquinazolinones, and a series of 2-arylquinazolinones were synthesized with moderate to good yields. This method was applied for the synthesis of a key intermediate of an IKK β inhibitor CU160 and a quinazolinone alkaloid 2-(1H-indol-3-yl) quinazolin-4(3H)-one. The mild and green synthesis scheme provides an effective alternative to the traditional synthesis of 2-arylquinazolinone.

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Section: Results and Discussionmentioning

confidence: 99%

Electrochemical C–H Arylation of Quinazolinone with Aryl Tetrafluoroborate Diazonium Salts in Aqueous Solution of Ionic Liquids

Ji,

Zhang,

Zhao

et al. 2023

ACS Sustainable Chem. Eng.

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“…Regioselective 1,2-functionalization of alkenes based on commercially accessed starting materials has proved to be a powerful tool for constructing elaborate carbon-based molecular skeletons. 5 This strategy successfully incorporates a wide array of functional groups across the carbon–carbon double bond. Despite these significant advancements, a limited range of practical protocols are available for the three-component regioselective 1,2-alkylarylation of alkenes to deliver relevant 1,1-diarylalkanes, especially those involving a C–H functionalization pathway.…”

mentioning

confidence: 99%

Three-component redox-neutral 1,2-alkylarylation of vinylarenes involving C–H functionalization enabled by copper catalysis

Yang

Wang

2023

Org. Chem. Front.

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Formal [2+1] Cycloadditions of a Metallacyclopentadiene Unit with Alkynes: Constructing Tetracyclic Conjugated Frameworks with Bridgehead Metals

Chu

Chen

et al. 2023

Chin. J. Chem.

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Comprehensive Summary Metallacyclopentadienes play a vital role in transition‐metal mediated and catalyzed cycloaddition reactions of alkynes. Though versatile reactions of metallacyclopentadienes with alkynes have been disclosed, [2+1] cycloadditions of metallacyclopentadienes and alkynes have never been discovered. In present work, we report the formal [2+1] cycloadditions of a metallacyclopentadiene unit with a broad scope of commercial alkynes, providing a facile strategy to construct tetracyclic conjugated compounds. The deuterated experiment indicates a metal vinylidene intermediate has been involved in [2+1] cycloaddition. Moreover, the electrophilic substitution reaction of the tetracyclic conjugated compound with the aid of density functional theory (DFT) calculated Fukui functions is investigated. These tetracyclic conjugated compounds exhibit broad absorption spectra in the whole visible region which could be employed as potential photovoltaic materials.

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Recent Progress in Aryl Radical-Mediated Cyclization of Unsaturated Bonds Based on Aryldiazonium Salts

Cited by 7 publications

References 87 publications

Electrochemical C–H Arylation of Quinazolinone with Aryl Tetrafluoroborate Diazonium Salts in Aqueous Solution of Ionic Liquids

Electrochemical C–H Arylation of Quinazolinone with Aryl Tetrafluoroborate Diazonium Salts in Aqueous Solution of Ionic Liquids

Three-component redox-neutral 1,2-alkylarylation of vinylarenes involving C–H functionalization enabled by copper catalysis

Formal [2+1] Cycloadditions of a Metallacyclopentadiene Unit with Alkynes: Constructing Tetracyclic Conjugated Frameworks with Bridgehead Metals

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