Sulfur‐Center‐Involved Photocatalyzed Reactions

Wang, Yuhong; Li, Yiming; Jiang, Xuefeng

doi:10.1002/asia.201800532

Cited by 54 publications

(15 citation statements)

References 133 publications

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“…Based on our longstanding interest in sulfur chemistry, we commenced our investigation by irradiating p ‐tolyl butyl sulfide ( 1 a ) with blue LEDs under an oxygen atmosphere in the presence of uranyl acetate as the catalyst. A solvent screen (Table S1, entries 1–4) showed that acetonitrile was beneficial for the generation of sulfone 3 a (43 %).…”

Section: Resultsmentioning

confidence: 74%

Selective Late‐Stage Oxygenation of Sulfides with Ground‐State Oxygen by Uranyl Photocatalysis

Rizvi

et al. 2019

Angew Chem Int Ed

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186

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Oxygenation is a fundamental transformation in synthesis. Herein, we describe the selective late‐stage oxygenation of sulfur‐containing complex molecules with ground‐state oxygen under ambient conditions. The high oxidation potential of the active uranyl cation (UO22+) enabled the efficient synthesis of sulfones. The ligand‐to‐metal charge transfer process (LMCT) from O 2p to U 5f within the O=U=O group, which generates a UV center and an oxygen radical, is assumed to be affected by the solvent and additives, and can be tuned to promote selective sulfoxidation. This tunable strategy enabled the batch synthesis of 32 pharmaceuticals and analogues by late‐stage oxygenation in an atom‐ and step‐efficient manner.

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Section: Resultsmentioning

confidence: 74%

Selective Late‐Stage Oxygenation of Sulfides with Ground‐State Oxygen by Uranyl Photocatalysis

Rizvi

et al. 2019

Angew Chem Int Ed

Self Cite

186

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“…The intermediates 6-substituted-3-mercapto-1,2,4-triazin-5-ones 1a-1e were prepared using known methods [15,21]. Sulfur atoms have a larger size and lower electronegativity than those of oxygen atoms, which makes the outer electron shell more prone to donate electrons, and results in most likely nucleophilic attack [22]. The intermediates 1a-1e underwent selectively rapid S-alkylation reaction, in which any possible N-, O-, or C-alkylation of the same substrate is much slower and hence negligible [23,24].…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, Characterization, and Biological Evaluation of Novel 7-Oxo-7H-thiazolo[3,2-b]-1,2,4-triazine-2-carboxylic Acid Derivatives

Cai

Xie

et al. 2020

Molecules

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A series of novel 7-oxo-7H-thiazolo[3,2-b]-1,2,4-triazine-2-carboxylic acid derivatives was synthesized in good yields by a multi-step procedure that included the generation of the S-alkylated derivatives from 6-substituted arylmethyl-3-mercapto-1,2,4-triazin-5-ones with ethyl 2-chloroacetoacetate, intramolecular cyclization with microwave irradiation, hydrolysis and amidation. All of the target compounds were fully characterized through 1H-NMR, 13C-NMR and HRMS spectra. The intramolecular cyclization occurred regioselectively at the N2-position of 1,2,4-triazine ring, which was confirmed by compound 3e using single-crystal X-ray diffraction analysis. The antibacterial and antitubercular activities of the target compounds were evaluated. Compared with Ciprofloxacin and Rifampicin, compounds 5d, 5f and 5g containing the terminal amide fragment exhibited broad spectrum antibacterial activity, and carboxylic acid derivatives or its corresponding ethyl esters had less effect on antibacterial properties. The most potent compound 5f also displayed excellent in vitro antitubercular activity against Mycobacterium smegmatis (minimum inhibitory concentration (MIC) = 50 μg/mL) and better growth inhibition activity of leucyl-tRNA synthetase (78.24 ± 4.05% at 15 μg/mL).

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“…Sulfur‐containing compounds serve important functions in organic synthesis, such as substrates, photosensitizers or hydrogen‐atom‐transfer (HAT) reagents and so on Thioethers as important building blocks in some important drugs or some biologically active compounds (shown in Figure ) have led to an increased awareness of researchers . At present, a variety of methods for the corresponding synthesis of thioethers are available in the literatures .…”

Section: Introductionmentioning

confidence: 99%

Efficient Thiolation of Alcohols Catalyzed by Long Chained Acid‐Functionalized Ionic Liquids under Mild Conditions

et al. 2019

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Thioethers as important building blocks have been usually found in organic synthesis. Herein, a series of long chained acid‐functionalized ionic liquids derived from pyrrolidine were applied for the thiolation of alcohols to synthesize different compounds containing thioether structures. This kind of ionic liquids exhibited higher efficiency than general ionic liquids based on imidazole, providing up to 99 % yield with [BsCtP][OTf] as the catalyst at room temperature for 0.25 h. The results indicated that the activities of the ionic liquids have relationship with the side chain length of ionic liquids based on pyrrolidine, anions and cations. The catalytic system had wide substrate scope and was applicable for the reaction of aromatic primary and secondary alcohols and thiols including aliphatic and aromatic thiols, benzothiazole‐2‐thiols and benzooxazole‐2‐thiols. Besides, there was no obvious change in activity of the catalyst after six runs. Thus, the catalytic system exhibited good recyclability. Additionally, carbocations should be the key intermediate and several functionalized groups of the ionic liquids have synergetic effect for the thiolation.

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Sulfur‐Center‐Involved Photocatalyzed Reactions

Cited by 54 publications

References 133 publications

Selective Late‐Stage Oxygenation of Sulfides with Ground‐State Oxygen by Uranyl Photocatalysis

Selective Late‐Stage Oxygenation of Sulfides with Ground‐State Oxygen by Uranyl Photocatalysis

Synthesis, Characterization, and Biological Evaluation of Novel 7-Oxo-7H-thiazolo[3,2-b]-1,2,4-triazine-2-carboxylic Acid Derivatives

Efficient Thiolation of Alcohols Catalyzed by Long Chained Acid‐Functionalized Ionic Liquids under Mild Conditions

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