A simple approach to indeno-coumarins <i>via</i> visible-light-induced cyclization of aryl alkynoates with diethyl bromomalonate

Li, Qingrui; Yin, Yunnian; Li, Yabo; Zhang, Jianye; Huang, Miaoliang; Kim, Jung Keun; Wu, Yangjie

doi:10.1039/c9qo00795d

Cited by 25 publications

(9 citation statements)

References 46 publications

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“…Bromomalonate 24 might undergo homolysis under this set of reaction conditions as an efficient radical initiator. α-Bromomalonates are known to form malonyl radicals via SET or an energy-transfer pathway. − In the energy-transfer pathway, bromine radicals are also formed; this raised doubts about the actual radical abstracting hydrogen from 1,3-dioxolane. In this regard, we performed a stoichiometric experiment between bromomalonate 24 and 1,3-dioxolane, and malonate 27 was formed in only 45% yield (unoptimized) (Scheme d).…”

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confidence: 91%

Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step

2021

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We describe a visible-light-promoted addition of a hydrogen atom and an acetal carbon toward various electrondeficient alkenes. 1,3-Dioxolane is converted to its radical species in the presence of persulfate and an iridium catalyst upon visible light irradiation, which then reacts with electron-deficient alkenes. The reaction operates via a radical chain mechanism, a less commonly observed pathway for this class of transformation. Hydrogen atom transfer from 1,3-dioxolane to α-malonyl radicals is corroborated by experimental and density functional theory studies.

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confidence: 91%

Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step

2021

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“…In the year 2019, Wu and group described a Visible‐light‐mediated triple‐domino cyclization of substrate 1 and diethyl bromomalonate to form indeno‐coumarins 38 with the use of K 2 HPO 4 .3H 2 O, [fac‐Ir(ppy) 3 ] [31] . The present reaction reveals that both bromine radical ( .…”

Section: Radical Cyclizationmentioning

confidence: 78%

Recent Advances in the Synthesis of Coumarin and Its Derivatives by Using Aryl Propiolates

Sharma

Dhayalan²,

Chatterjee

et al. 2022

ChemistrySelect

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Coumarins (2H‐1‐benzopyran‐2‐one) are a class of natural products extracted from plant with a broad range of biological activities like antitubercular, anti‐inflammatory, anticancer, anticonvulsant, neuroprotective, antiviral, antifungal, antibacterial, antihyperglycemic, anticoagulant, antihypertensive, antiadipogenic, and antioxidant, effects. Therefore, the synthesis of coumarin and its derivatives has become amongst the most attractive compounds over the last two decades in the growth of improved synthetic methods to form various coumarins derivatives. Amongst the reported methods for the construction of coumarins, the pendant arylpropiolate scaffolds served as a highly appealing precursor for coumarins in a single step. This review article describes recent updates on the construction of coumarins using arylpropiolate as substrates.

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“…In 2019, Wu's group reported a unique method for the synthesis of indeno‐coumarins 34 from 3‐phenylpropiolates 1 by employing fac ‐Ir(ppy) 3 , BrCH(CO 2 Et) 2 33 , and CsOAc under the reaction conditions (Scheme 13). [29] The aryl 3‐phenylpropiolates having electron‐withdrawing groups at para ‐position reacted poorly in comparison to the electron‐donating ones, while the ortho ‐substituted aryl 3‐phenylpropiolates were found inactive due to steric repulsions. Furthermore, two regioisomers ( 34 a , 34 b ) in moderate yields were obtained from meta ‐substituted aryl alkynoates.…”

Section: Cyclization Approach To Functionalized Coumarinsmentioning

confidence: 99%

Visible Light‐Induced Synthesis of Functionalized Coumarins

Singh

Sharma

2021

Adv Synth Catal

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Functionalized coumarins are privileged scaffolds which display diverse pharmacological and physiological activities, and a myriad of applications in medical science and biomedical research. Owing to these multifarious activities of coumarins, synthetic chemists are actively engaged in developing new and superior methods for their synthesis. In the last decade, the synthesis of functionalized coumarins via visible light-induced methodologies has turned into one of the most significant and fundamental missions in organic synthesis. This review covers the literature on the synthesis of functionalized coumarins under visible light-assisted methodologies. 3.6. 4-Chloro-3-Nitrocoumarin as Substrate 3.7. 1-Bromo-2H-Phenaleno[1,2,3-de]chromen-2-Ones as Substrate 4.Conclusions

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A simple approach to indeno-coumarins via visible-light-induced cyclization of aryl alkynoates with diethyl bromomalonate

Abstract: Visible-light-induced triple-domino cyclization between aryl alkynoates and diethyl bromomalonate was developed for the synthesis of indeno-coumarins.

Cited by 25 publications

References 46 publications

Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step

Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step

Recent Advances in the Synthesis of Coumarin and Its Derivatives by Using Aryl Propiolates

Visible Light‐Induced Synthesis of Functionalized Coumarins

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