Visible Light‐ and Heat‐Promoted C−O Coupling Reaction of Phenols and Aryl Halides

Yang, Qing‐Qing; Liu, Na; Yan, Jiaying; Ren, Zhi‐Lin; Wang, Long

doi:10.1002/ajoc.201900666

Cited by 27 publications

(14 citation statements)

References 123 publications

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“…Recently, advances in visible-light photoredox activation of sulfonyl chlorides have been gained . Inspired by these seminal works, we hypothesized that visible-light photocatalysis could be used to form sulfur-centered radical intermediates under mild conditions from readily available sulfonyl chlorides. We anticipated that sulfur-centered radical intermediates could be further captured by alkenes via radical addition across the double bond.…”

Section: Results and Discussionmentioning

confidence: 99%

Visible-Light Photoredox-Catalyzed Sulfonyl Lactonization of Alkenoic Acids with Sulfonyl Chlorides for Sulfonyl Lactone Synthesis

Rao

Chen

et al. 2021

J. Org. Chem.

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A visible-light photoredox-catalyzed sulfonyl lactonization of unsaturated carboxylic acids with sulfonyl chlorides is described. This reaction features good functional group tolerance and a broad substrate scope, providing a simple and efficient protocol to access a wide range of sulfonyl lactones in high to excellent yields. Preliminary mechanistic investigations suggested that a free-radical pathway should be involved in the process.

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Section: Results and Discussionmentioning

confidence: 99%

Visible-Light Photoredox-Catalyzed Sulfonyl Lactonization of Alkenoic Acids with Sulfonyl Chlorides for Sulfonyl Lactone Synthesis

Rao

Chen

et al. 2021

J. Org. Chem.

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“…To further test the photocatalytic ability of 1a in other transformations such as etherification reaction. , We first utilized 1a to catalyze the photodecarboxylative alkylations of substituted thiophenol derivatives 5 (Scheme ). The light-induced alkylation of 5 with 3 catalyzed by 1a proceeded smoothly.…”

Section: Resultsmentioning

confidence: 99%

Deprotonated Salicylaldehyde as Visible Light Photocatalyst

Zhuang

Kang

2020

J. Org. Chem.

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Salicylaldehyde is established as an efficient visible light photocatalyst for the first time. Compared to other simple aldehyde analogies, salicylaldehyde has a unique deprotonative red-shift from 324 to 417 nm and gives rise to the remarkable increase of fluorescence quantum from 0.0368 to 0.4632, thus enabling salicylaldehyde as a visible light (>400 nm) photocatalyst. The experimental investigations suggest that the reactive radical species are generated by sensitization of the substrates by the deprotonated salicylaldehyde through an energy-transfer pathway. Consequently, the C–C cleaving alkylation reactions of N-hydroxyphthalimide esters proceed smoothly in the presence of as low as 1 mol % of salicylaldehyde under the visible-light irradiation, affording desired alkylation products with up to 99% yields. Application in visible-light induced aerobic oxidation of N-alkylpyridinium salts is also reported.

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“…Heat is a kind of energy that can change many things, such as accelerating the movement of molecules, increasing chemical reaction rates, and so on. − For biological systems, hyperthermia can lead to breaking of proteins and DNA, which may finally result in the death of cells or even the death of living creatures. Therefore, researchers utilize heat to kill cancer cells, pathogens, and other components harmful to the human body. − Besides, some compounds can respond to heat to make changes in structure and shape, such as thermosensitive polymers, or to decompose at high temperature. − Taking advantage of this, many drug delivery systems to improve the controllability and specificity of drug release have been developed. − Therefore, the generation of heat plays an important role in the biological and biomedical areas.…”

Section: Introductionmentioning

confidence: 99%

Photothermal Conjugated Polymers and Their Biological Applications in Imaging and Therapy

Zhang

Wang

Feng

2020

ACS Appl. Polym. Mater.

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Conjugated polymers have been developed as candidates with great potential for biological and biomedical applications due to the excellent properties, including strong light absorption, high photostability, good biocompatibility, and tunable spectra. By design of the backbone structure, photothermal polymers can be obtained with narrow band gaps and high photothermal conversion efficiencies. As promising photothermal agents, photothermal conjugated polymers have been synthesized to be water-soluble or in the form of nanoparticles for biological applications of imaging, phototherapy, and photoactivation. This review summarizes the recent (2018–2020) progress on photothermal conjugated polymers with regard to molecular design, preparation, and photothermal biological applications, especially NIR imaging (fluorescence and photoacoustic)-guided photothermal therapy and combined therapy for cancer and antibacterial photothermal therapy. Further challenges and the outlook for photothermal conjugated polymers in biological applications are also discussed at the end.

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Visible Light‐ and Heat‐Promoted C−O Coupling Reaction of Phenols and Aryl Halides

Cited by 27 publications

References 123 publications

Visible-Light Photoredox-Catalyzed Sulfonyl Lactonization of Alkenoic Acids with Sulfonyl Chlorides for Sulfonyl Lactone Synthesis

Visible-Light Photoredox-Catalyzed Sulfonyl Lactonization of Alkenoic Acids with Sulfonyl Chlorides for Sulfonyl Lactone Synthesis

Deprotonated Salicylaldehyde as Visible Light Photocatalyst

Photothermal Conjugated Polymers and Their Biological Applications in Imaging and Therapy

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