Visible Light‐Induced Decarboxylative Acylarylation of Phenyl Propiolates with α‐Oxocarboxylic Acids to Coumarins Catalyzed by Hypervalent Iodine Reagents under Transition Metal‐Free Conditions

Yang, Shuai; Tan, Hui; Ji, Wangqin; Zhang, Xiang-Biao; Li, Pinhua; Wang, Lei

doi:10.1002/adsc.201600721

Cited by 69 publications

(15 citation statements)

References 109 publications

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“…Wang et al. also reported a radical cyclization with in‐situ‐generated hypervalent iodine II (Figure a) with blue LED (450 nm) irradiation . According to the Grotthuss–Draper law, light must be absorbed by a substrate or catalyst to initiate a photoreaction.…”

Section: Introductionmentioning

confidence: 99%

A Direct S₀→T_n Transition in the Photoreaction of Heavy‐Atom‐Containing Molecules

et al. 2020

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According to the Grotthuss–Draper law, light must be absorbed by a substrate to initiate a photoreaction. There have been several reports, however, on the promotion of photoreactions using hypervalent iodine during irradiation with light from a non‐absorbing region. This contradiction gave rise to a mystery regarding photoreactions involving hypervalent iodine. We demonstrated that the photoactivation of hypervalent iodine with light from the apparently non‐absorbing region proceeds via a direct S0→Tn transition, which has been considered a forbidden process. Spectroscopic, computational, and synthetic experimental results support this conclusion. Moreover, the photoactivation mode could be extended to monovalent iodine and bromine, as well as bismuth(III)‐containing molecules, providing new possibilities for studying photoreactions that involve heavy‐atom‐containing molecules.

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Section: Introductionmentioning

confidence: 99%

A Direct S₀→T_n Transition in the Photoreaction of Heavy‐Atom‐Containing Molecules

et al. 2020

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“…Besides benzaldehydes and aryl acyl chlorides, the synthesis of 3-acyl-4-arylcoumarins 21 from phenyl 3phenylpropiolates 1 by employing α-oxocarboxylic acids 20 as acyl radical precursors was developed by Wang and co-workers (Scheme 9(b)). [22] Notably, the reaction neither required a photocatalyst nor an oxidant, and had broad substrate scope and high efficiency. Interestingly, para-and meta-substituted αoxocarboxylic acids gave better yields compared to ortho-substituted ones, while 2-oxo-3-phenylpropanoic acid did not participate in the reaction probably due to a lesser stability of the alkyl acyl radical than the aryl acyl radical.…”

Section: Functionalized Coumarin Synthesis Via Cà C Bond Formationmentioning

confidence: 99%

“…Besides benzaldehydes and aryl acyl chlorides, the synthesis of 3‐acyl‐4‐arylcoumarins 21 from phenyl 3‐phenylpropiolates 1 by employing α ‐oxocarboxylic acids 20 as acyl radical precursors was developed by Wang and co‐workers (Scheme 9(b)) [22] . Notably, the reaction neither required a photocatalyst nor an oxidant, and had broad substrate scope and high efficiency.…”

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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“…α-Oxo-carboxylic acids were used as the radical sources, which could undergo decarboxylation to afford carbonyl radicals by iodide catalyst. The desired coumarins were obtained in 51%-81% yields [137]. Aryl aldehydes and aryl carbonyl chlorides could also be used as carbonyl radical precursors.…”

Section: Imidoyl Radical or Carbonyl Radical Precursorsmentioning

confidence: 99%

Visible light promoted difunctionalization reactions of alkynes

Ren

2019

Chinese Journal of Catalysis

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Visible light promoted difunctionalization of alkynes is reviewed. The difunctionalization reaction is achieved by different reagents. Radicals such as carbon (sp 3), carbon (sp 2), and other heteroatom (P, S, N, Se, O, and halide) radicals initiated by visible light can undergo radical addition to a carbon-carbon triple bond. Upon further transformation, the desired difunctionalized products are obtained. Some organometallic complexes can be activated by visible light; the difunctionalization of alkynes is catalyzed by these species. Other reagents like 1,3-dipole precursors could also react with alkynes to give difunctionalization products; here, the 1,3-dipole derivatives are obtained by visible light photocatalysis. So far, the strategy has been succeeded in the formation of CC bonds and C-X bonds. Several valuable chemical skeletons have been constructed under mild conditions. However, high regio-and stereoselectivities in some direct difunctionalization methodologies are yet to be achieved.

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Visible Light‐Induced Decarboxylative Acylarylation of Phenyl Propiolates with α‐Oxocarboxylic Acids to Coumarins Catalyzed by Hypervalent Iodine Reagents under Transition Metal‐Free Conditions

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Cited by 69 publications

References 109 publications

A Direct S₀→T_n Transition in the Photoreaction of Heavy‐Atom‐Containing Molecules

A Direct S₀→T_n Transition in the Photoreaction of Heavy‐Atom‐Containing Molecules

Visible Light‐Induced Synthesis of Functionalized Coumarins

Visible light promoted difunctionalization reactions of alkynes

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Visible Light‐Induced Decarboxylative Acylarylation of Phenyl Propiolates with α‐Oxocarboxylic Acids to Coumarins Catalyzed by Hypervalent Iodine Reagents under Transition Metal‐Free Conditions

Abstract: No Abstractmagnified image

Cited by 69 publications

References 109 publications

A Direct S0→Tn Transition in the Photoreaction of Heavy‐Atom‐Containing Molecules

A Direct S0→Tn Transition in the Photoreaction of Heavy‐Atom‐Containing Molecules

Visible Light‐Induced Synthesis of Functionalized Coumarins

Visible light promoted difunctionalization reactions of alkynes

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A Direct S₀→T_n Transition in the Photoreaction of Heavy‐Atom‐Containing Molecules

A Direct S₀→T_n Transition in the Photoreaction of Heavy‐Atom‐Containing Molecules