Site-selective phenol acylation mediated by thioacids<i>via</i>visible light photoredox catalysis

Shi, Lili; Liu, Hongxin; Huo, Luqiong; Dang, Yaqian; Wang, Yu; Yang, Bao; Qiu, Shaofu; Tan, Haibo

doi:10.1039/c8qo00041g

Cited by 9 publications

(11 citation statements)

References 63 publications

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“…Then, we established diglyme as the reaction solvent for the acetylation of phenol compounds. Although the reaction proceeded smoothly, the observed low yield was presumably due to the weaker nucleophilicity of the hydroxy group compared to the amino functional groups [26] . Increasing reaction temperature and extending reaction time improved reaction yields.…”

Section: Resultsmentioning

confidence: 98%

“…Therefore, we concluded that the reaction conditions for esterification of phenols work as well as for amidation. Tan and co‐workers also realized the amidation reaction of amine compounds [18] and the esterification reaction of phenolic compounds [26] by fine‐tuning the reaction conditions. As a result, we used 4 ab as a model substrate and 2 as the acylating reagent, and the reaction was carried out under a CO 2 atmosphere.…”

Section: Resultsmentioning

confidence: 99%

“…Although the reaction proceeded smoothly, the observed low yield was presumably due to the weaker nucleophilicity of the hydroxy group compared to the amino functional groups. [26] Increasing reaction temperature and extending reaction time improved reaction yields. When the temperature was increased to 100 °C, the yield reached 54 % (Table S2, entries 3-5).…”

Section: Chemsuschemmentioning

confidence: 99%

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CO₂‐Promoted Direct Acylation of Amines and Phenols by the Activation of Inert Thioacid Salts

Wang

Liu

et al. 2022

ChemSusChem

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Herein a carbon dioxide-promoted synthetic approach for the direct amidation between unactivated thioacid salts and amines under mild conditions was developed for a wide range of substrates. The method afforded amides in good to excellent yields under transition-metal-free and activation-reagent-free conditions, in sharp contrast to early methodologies on amide synthesis based on transition-metal catalysis. The method offered a greener and transition metal-free protocol applicable to pharmaceuticals preparations. Phenolic compounds were also found to be suitable acylation substrates with potassium thiosulfide KHS as the only byproduct. Moreover, this approach was applied to amide synthesis of valuable bio-active molecules such as moclobemide, melatonin, and a fungicide. Insights into the reaction mechanism involving carbon dioxide were provided through NMR spectroscopy and computational calculations. A plausible mechanism was proposed that involves weak interactions between carbon dioxide and potassium thioacetate in a dynamic equilibrium state formation of a six-membered ring.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Section: Chemsuschemmentioning

confidence: 99%

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CO₂‐Promoted Direct Acylation of Amines and Phenols by the Activation of Inert Thioacid Salts

Wang

Liu

et al. 2022

ChemSusChem

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“…The product was isolated following the general procedure as a colorless solid (31.7 4-Acetylphenyl Benzoate (4g). 42 The representative procedure was followed using 1-(4-bromophenyl)ethan-1-one 2g (0.2 mmol) and benzoic acid 3a (0.4 mmol). The product was isolated following the general procedure as a colorless solid (25.1 mg, 52% yield, mp = 130.2− 132.4 °C).…”

Section: ■ Conclusionmentioning

confidence: 99%

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

Zhang

Xia

et al. 2021

J. Org. Chem.

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Energy transfer plays a special role in photocatalysis by utilizing the potential energy of the excited state through indirect excitation, in which a photosensitizer determines the thermodynamic feasibility of the reaction. Bioinspired by the energy-transfer ability of natural product cercosporin, here we developed a green and highly efficient organic photosensitizer HiBRCP (hexaisobutyryl reduced cercosporin) through structural modification of cercosporin. After structural manipulation, its triplet energy was greatly improved, and then, it could markedly promote the efficient geometrical isomerization of alkenes from the E-isomer to the Z-isomer. Moreover, it was also effective for energy-transfer-mediated organometallic catalysis, which allowed realization of the cross-coupling of aryl bromides and carboxylic acids through efficient energy transfer from HiBRCP to nickel complexes. Thus, the study on the relationship between structural manipulation and their photophysical properties provided guidance for further modification of cercosporin, which could be applied to more meaningful and challenging energy-transfer reactions.

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“…(106)] was recently achieved by the same group, see Scheme 42. [67] The Oxygenation of Sulfides Since 1962, the photo-oxidation of sulfidesh as been extensively studied, but with energy-inefficient light sources, such as halogen lamps and Xenon lamps. [68] Recently,l ow-wattage condensed fluorescent lamps (CFLs), light-emitting diodes (LEDs), and photoelectrosynthesis model cells [69] have been used to realize the oxygenation of sulfide.…”

Section: Carbon-sulfur Bond Cleavagementioning

confidence: 99%

Sulfur‐Center‐Involved Photocatalyzed Reactions

Wang

Jiang

2018

Chemistry An Asian Journal

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Sulfur-containing compounds (SCCs) exist widely in, for example, natural sources, pharmaceuticals, materials, and foods. Their multifarious functions have stimulated scientists to construct them in greener and more efficient ways and further exploit their properties. Different photosensitizers with sulfur atoms have been developed and exploited. Furthermore, SCCs display excellent ability in hydrogen-atom-transfer reactions. In addition to acting as catalysts, SCCs can also be efficiently transformed under visible-light-promoted conditions. Bond dissociation and oxygenation reactions that involve sulfur centers are emphasized here.

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Site-selective phenol acylation mediated by thioacidsviavisible light photoredox catalysis

Cited by 9 publications

References 63 publications

CO₂‐Promoted Direct Acylation of Amines and Phenols by the Activation of Inert Thioacid Salts

CO₂‐Promoted Direct Acylation of Amines and Phenols by the Activation of Inert Thioacid Salts

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

Sulfur‐Center‐Involved Photocatalyzed Reactions

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Site-selective phenol acylation mediated by thioacidsviavisible light photoredox catalysis

Cited by 9 publications

References 63 publications

CO2‐Promoted Direct Acylation of Amines and Phenols by the Activation of Inert Thioacid Salts

CO2‐Promoted Direct Acylation of Amines and Phenols by the Activation of Inert Thioacid Salts

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

Sulfur‐Center‐Involved Photocatalyzed Reactions

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Product

Resources

About

CO₂‐Promoted Direct Acylation of Amines and Phenols by the Activation of Inert Thioacid Salts

CO₂‐Promoted Direct Acylation of Amines and Phenols by the Activation of Inert Thioacid Salts