Facile and efficient synthesis of hydroxyalkyl esters from cyclic acetals through aerobic photo-oxidation using anthraquinone-2-carboxylic acid

Yamaguchi, T.; Kudo, Yasuhisa; Hirashima, Shin‐ichi; Yamaguchi, Eiji; Tada, Norio; Miura, Tsuyoshi; Itoh, Akichika

doi:10.1016/j.tetlet.2015.02.104

Cited by 14 publications

(7 citation statements)

References 36 publications

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“…A related application involved the oxidation of cyclic acetals in the presence of anthraquinone‐2‐carboxylic acid under visible light irradiation conditions to give the corresponding hydroxyalkyl esters . The same photocatalyst could be also applied to the one‐pot epoxidation of alkenes.…”

Section: Direct Hat Approachesmentioning

confidence: 99%

Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

2017

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The adoption of hydrogen atom transfer (HAT) in a photocatalytic approach, in which an excited catalyst is responsible for substrate activation, offers unique opportunities in organic synthesis, enabling the straightforward activation of R–H (R = C, Si, S) bonds in desired reagents. Either a direct strategy, based on the intrinsic reactivity of a limited number of photocatalysts in the excited state, or an indirect one, in which a photocatalytic cycle is used for the generation of a thermal hydrogen abstractor, can be exploited. This microreview summarizes the most recent advances (mainly from the last two years) in this rapidly developing area of research, collecting the selected examples according to the nature of the species promoting the HAT process. From the synthetic point of view, this area has led to the development of a plethora of strategies for C–C, C–Si, C–N, C–S, and C–halogen (particularly, fluorine) bond formation, as well as for oxidation reactions.

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Section: Direct Hat Approachesmentioning

confidence: 99%

Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

2017

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“…Optimization of the reaction conditions was conducted using cyclooctane 1a as a starting substance (Table ). Among the aryl ketones examined, 2-ClAQ − afforded a higher yield of the expected adduct 2a (54%, entry 1) than did benzophenone (40%, entry 2) or 4-benzoylpyridine ,, (42%, entry 3). It is important to note that the present transformation could be promoted merely by a catalytic amount of 2-ClAQ (0.1 equiv).…”

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confidence: 99%

Alkylation of Nonacidic C(sp³)–H Bonds by Photoinduced Catalytic Michael-Type Radical Addition

et al. 2016

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Photoinduced catalytic Michael-type radical addition was achieved via olefin insertion into a nonacidic C(sp)-H bond, utilizing 2-chloroanthraquinone as a C-H bond-cleaving catalyst and 1,1-bis(phenylsulfonyl)ethylene as an olefinic substrate. The present radical protocol allows carbon chain extension stemming from nonacidic C-H bonds, which complements alkylation at acidic C-H bonds under ionic conditions and installs the active methine site that acts as a versatile synthetic handle for further transformations.

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“…In the last decade, some researchers have begun to employ AQs in visible‐light induced, catalytic photooxidations obtaining products such as carboxylic acids, gem ‐diols, aromatic methyl esters, phenols, diacylamines, epoxides, and hydroxyalkyl esters. This activation involves either hydrogen‐atom or electron transfer …”

Section: Applications Of Aqs In Organic Synthesismentioning

confidence: 99%

“…Another example of the use of AQs in photooxidative processes is the preparation of hydroxyalkyl esters from 1,3‐dioxolanes and 1,3‐dioxanes using 2‐CO 2 H‐AQ in EtOAc and O 2 with a fluorescent lamp for 3 h (Scheme ) . The products were obtained in acceptable yields, tolerating methoxy and chloro substituents on the aromatic ring, with yields of 49–80 %.…”

Section: Applications Of Aqs In Organic Synthesismentioning

confidence: 99%

Anthraquinones: Versatile Organic Photocatalysts

et al. 2020

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Anthraquinones (AQs) constitute the largest group of natural pigments, are commonly found in dyes, and are widely used in the textile industry due their photostability. They combine high absorptivity in the visible region with high excited‐state reduction potentials, making them effective acceptors of electrons and hydrogen atoms. AQs can be employed as organic catalysts in photooxidation reactions as well to produce reactive oxygen species (ROS). All these methods feature green chemistry aspects such as avoiding heavy metals, reducing waste, using inexpensive reagents, employing environmentally low‐impact solvents, and oxidizing with O2. This review covers the application of AQs in photoredox catalysis.

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Facile and efficient synthesis of hydroxyalkyl esters from cyclic acetals through aerobic photo-oxidation using anthraquinone-2-carboxylic acid

Cited by 14 publications

References 36 publications

Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

Alkylation of Nonacidic C(sp³)–H Bonds by Photoinduced Catalytic Michael-Type Radical Addition

Anthraquinones: Versatile Organic Photocatalysts

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Facile and efficient synthesis of hydroxyalkyl esters from cyclic acetals through aerobic photo-oxidation using anthraquinone-2-carboxylic acid

Cited by 14 publications

References 36 publications

Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

Alkylation of Nonacidic C(sp3)–H Bonds by Photoinduced Catalytic Michael-Type Radical Addition

Anthraquinones: Versatile Organic Photocatalysts

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Alkylation of Nonacidic C(sp³)–H Bonds by Photoinduced Catalytic Michael-Type Radical Addition