Ring-opening/annulation reaction of cyclopropyl ethanols: concise access to thiophene aldehydes <i>via</i> C–S bond formation

Wang, Ting; An, Zhenyu; Qi, Zhenjie; Zhuang, Daijiao; Chang, Aosheng; Yang, Yunxia; Yan, Rulong

doi:10.1039/c9qo01014a

Cited by 13 publications

(4 citation statements)

References 69 publications

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“…The S-centered, blue radical species S 3 ̇ – has recently attracted significant interest in organic synthesis . Despite remarkable advances in sulfur-mediated Willgerodt-type C–N bond formation, direct incorporations of the trisulfur radical into alkenyl double bonds are rare . Liu et al developed a method using K 2 S/DMF as a S 3 ̇ – generator, which is trapped by the α,β-unsaturated N -sulfonylimines to produce isothiazoles .…”

mentioning

confidence: 99%

Trisulfur-Radical-Anion-Triggered C(sp²)–H Amination of Electron-Deficient Alkenes

et al. 2020

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A trisulfur-radical-anion (S3̇–)-triggered C(sp2)–H amination of α,β-unsaturated carbonyl derivatives with simple amines has been demonstrated. This protocol provides convenient access to a variety of synthetically valuable N-unprotected and secondary β-enaminones with absolute Z selectivity and tertiary β-enaminones with E selectivity. Mechanistic probe and electronic structure theory calculations suggest that S3̇– initiates the nucleophilic attacks via a thiirane intermediate.

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confidence: 99%

Trisulfur-Radical-Anion-Triggered C(sp²)–H Amination of Electron-Deficient Alkenes

et al. 2020

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“…In 2019, Yan's group reported the synthesis of thiophene aldehydes 154 using readily available cyclopropyl ethanols 153 and K 2 S (Scheme 12). [32] The construction of double CÀ S bonds was achieved in one-pot through CÀ C bond cleavage. It proceeded in mild conditions with good functional group tolerance.…”

Section: Potassium Sulfidementioning

confidence: 99%

Syntheses of Thiophenes – Recent Advances

Peng,

Yin,

et al. 2024

Asian J Org Chem

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Thiophene, as an important sulfur‐containing heterocyclic, is widely used in pharmaceuticals, functional materials, and natural products. Furthermore, thiophene is of great interest to synthetic chemists due to its diverse reactivities. Over the past few decades, many synthetic strategies are developed for functionalized thiophenes. Several reviews have been reported. However, there is no review on thiophene synthesis summarized based on the sulfur sources. The current review envisioned to summary the synthesis methods for thiophene with the respect of sulfur sources and give support for choose the appropriate tools to obtain thiophene substrates.

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“…Full experimental procedures, characterization data, and copies of NMR spectra are included. The authors have cited additional references within the Supporting Information [25–29] …”

Section: Supporting Informationmentioning

confidence: 99%

“…The authors have cited additional references within the Supporting Information. [25][26][27][28][29]…”

Section: Supporting Informationmentioning

confidence: 99%

Halogen Promoted Desulfurative Cleavage of Cyclopropylmethyl Thioethers and Amination of the Formed Cyclopropylcarbinyl Cations

Marín‐Díaz,

Martínez‐Núñez,

Sanz

et al. 2024

Eur J Org Chem

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Cyclopropylmethyl sulfides react with N‐fluorosulfonimide (NFSI) or molecular iodine, enabling C–S cleavage to generate cyclopropylcarbinyl cations, which evolve through cyclopropane ring‐opening reactions into homoallyl cations suitable to react with nucleophiles present in the reaction media. This desulfurative cleavage of cyclopropylmethyl thioethers under non‐acidic conditions facilitates homoallylation of N‐based nucleophiles such as alkyl or aryl amines as well as sulfonimides through a one‐pot protocol in one or two steps depending on the nucleophile. The reaction is initiated by a halogen‐sulfur bond that causes C–S bond cleavage. Moreover, the reaction with iodine proceeds through homoallyl iodide intermediates.

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Ring-opening/annulation reaction of cyclopropyl ethanols: concise access to thiophene aldehydes via C–S bond formation

Abstract: The synthesis of thiophene aldehydes from easily available cyclopropyl ethanol derivatives and potassium sulfide has been developed.

Cited by 13 publications

References 69 publications

Trisulfur-Radical-Anion-Triggered C(sp²)–H Amination of Electron-Deficient Alkenes

Trisulfur-Radical-Anion-Triggered C(sp²)–H Amination of Electron-Deficient Alkenes

Syntheses of Thiophenes – Recent Advances

Halogen Promoted Desulfurative Cleavage of Cyclopropylmethyl Thioethers and Amination of the Formed Cyclopropylcarbinyl Cations

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Ring-opening/annulation reaction of cyclopropyl ethanols: concise access to thiophene aldehydes via C–S bond formation

Abstract: The synthesis of thiophene aldehydes from easily available cyclopropyl ethanol derivatives and potassium sulfide has been developed.

Cited by 13 publications

References 69 publications

Trisulfur-Radical-Anion-Triggered C(sp2)–H Amination of Electron-Deficient Alkenes

Trisulfur-Radical-Anion-Triggered C(sp2)–H Amination of Electron-Deficient Alkenes

Syntheses of Thiophenes – Recent Advances

Halogen Promoted Desulfurative Cleavage of Cyclopropylmethyl Thioethers and Amination of the Formed Cyclopropylcarbinyl Cations

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Product

Resources

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Trisulfur-Radical-Anion-Triggered C(sp²)–H Amination of Electron-Deficient Alkenes

Trisulfur-Radical-Anion-Triggered C(sp²)–H Amination of Electron-Deficient Alkenes