Brønsted acid-promoted three-component reaction of 2-methoxythiophene, sulfinates and water: Synthesis of γ-mercapto-β-sulfonyl esters

Chen, Xianlie; Luo, Yixin; Zeng, Qingle

doi:10.1016/j.tetlet.2022.153884

Cited by 3 publications

(1 citation statement)

References 17 publications

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“…[20] There is only one ring-opening reaction of vinyl small ring compounds, namely vinyl oxiranes, with Ntosylhydrazones (Scheme 1, Equation c). [21] Therefore, as our ongoing study on palladium catalyzed reactions [22][23] and organosulfur chemistry, [24][25] we intended to study the palladiumcatalyzed ring-opening addition reaction of activated vinyl cyclopropanes with N-tosylhydrazones.…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Ring‐Opening Addition of Activated Vinyl Cyclopropanes with N‐Tosylhydrazones

et al. 2023

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Ring‐opening addition reaction of activated vinyl cyclopropanes with N‐tosylhydrazones in the presence of palladium(0) and triphenylphosphine affords N‐tosylhydrazone butenylmalonate compounds. Aromatic aldehyde‐derived N‐tosylhydrazones produced terminal and internal N‐allylated products, in which the terminal products are the main. While ketone‐derived tosylhydrazones produced only terminal addition products. The transformation relationship of the terminal and internal N‐allylated products in the reaction was also observed. A reasonable mechanism is proposed based on preliminary experimental results.

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Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Ring‐Opening Addition of Activated Vinyl Cyclopropanes with N‐Tosylhydrazones

et al. 2023

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White Light/NIS‐Promoted Aminoselenylation of Alkenes by Using N‐Tosylhydrazones

2023

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A white light/iodosuccinimide (NIS)‐promoted three component reaction of alkenes, N‐sulfonylhydrazones, and diorganyl diselenides for synthesis of organylselenylethyl sulfonylhydrazones under air is disclosed. This intermolecular aminoselenylation of alkenes using N‐tosylhydrazones as nitrogen source was performed under mild conditions and well tolerated for common groups. In addition, heteroaryl and aliphatic diselenides also gave the target compounds. Gram‐scale reaction also carried out smoothly. This protocol has a wide range of substrates and affords moderate to high yields and excellent regioselectivities. The photoactive intermediates from the interaction between NIS and diphenyl diselenide was detected by UV‐visible absorption spectra, which matches the wavelength of the applied white LED. A reasonable mechanism was proposed based on UV‐visible light experiments and control experiments.

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Indium(III)‐Catalyzed Three Component Reaction of N‐Bromosuccinimide, Alkenes and N‐Tosylhydrazones

Luo,

Zhou,

Nkingwa

et al. 2024

Eur J Org Chem

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A three‐component reaction involving alkenes, N‐sulfonylhydrazones, and N‐bromosuccinimide (NBS) is described that uses Indium(III) triflate for the synthesis of bromoethyl sulfonyl hydrazones. Using N‐tosylhydrazones as a nitrogen source and NBS as a bromine source, this intermolecular aminobromination of alkenes is carried out under air in mild conditions. A mechanism of electrophilic addition is proposed based on the GC‐MS analytical result.

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Brønsted acid-promoted three-component reaction of 2-methoxythiophene, sulfinates and water: Synthesis of γ-mercapto-β-sulfonyl esters

Cited by 3 publications

References 17 publications

Palladium‐Catalyzed Ring‐Opening Addition of Activated Vinyl Cyclopropanes with N‐Tosylhydrazones

Palladium‐Catalyzed Ring‐Opening Addition of Activated Vinyl Cyclopropanes with N‐Tosylhydrazones

White Light/NIS‐Promoted Aminoselenylation of Alkenes by Using N‐Tosylhydrazones

Indium(III)‐Catalyzed Three Component Reaction of N‐Bromosuccinimide, Alkenes and N‐Tosylhydrazones

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