Visible Light‐Induced Regioselective Decarboxylative Alkylation of the C(<i>sp</i><sup>2</sup>)−H Bonds of Non‐Aromatic Heterocycles

Liu, Lixin; Pan, Neng; Sheng, Wei; Su, Lebin; Liu, Long; Dong, Jianyu; Zhou, Yongbo; Yin, Shuang‐Feng

doi:10.1002/adsc.201900572

Cited by 78 publications

(24 citation statements)

References 88 publications

(58 reference statements)

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“…In the same year, Zhou's groups reported a similar strategy for the synthesis of C-3 alkylated coumarins 113 by comprising Ru(bpy) 3 Cl 2 as a photocatalyst, DABCO as a base, and DMAc as a solvent under sunlight (Scheme 35 (b)). [65] The substrate scope implied that primary, secondary (acyclic and cyclic), and tertiary alkyl N-hydroxyphthalimide esters proved as suitable substrates. While lower yields were obtained from tertiary alkyl N-hydroxyphthalimide esters probably due to difficult addition of the sterically bulky alkyl radicals to the carbon-carbon double bond of the coumarins.…”

Section: H-1-benzopyran-2-ones As Substratesmentioning

confidence: 99%

“…In the same year, Zhou's groups reported a similar strategy for the synthesis of C‐3 alkylated coumarins 113 by comprising Ru(bpy) 3 Cl 2 as a photocatalyst, DABCO as a base, and DMAc as a solvent under sunlight (Scheme 35(b)) [65] . The substrate scope implied that primary, secondary (acyclic and cyclic), and tertiary alkyl N ‐hydroxyphthalimide esters proved as suitable substrates.…”

Section: Functionalization Of Coumarin Scaffold (Coumarins As Substrates)mentioning

confidence: 99%

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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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Section: H-1-benzopyran-2-ones As Substratesmentioning

confidence: 99%

Section: Functionalization Of Coumarin Scaffold (Coumarins As Substrates)mentioning

confidence: 99%

Visible Light‐Induced Synthesis of Functionalized Coumarins

Singh

Sharma

2021

Adv Synth Catal

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“…Subsequently, Liu et al described a similar Ru(bpy) 3 Cl 2catalyzed alkylation of coumarins 35 (Scheme 23). [58] Importantly, the method was shown to be applicable for the alkylation of other non-aromatic heterocycles, such as quinolinones and quinoxalinones providing the corresponding alkylated products 36 in moderate yields. NHPI esters derived from naturally occurring stearic acid and pharmaceutical molecule gemfibrozil were successfully utilized in the alkylation of coumarins providing the corresponding products in 50% and 40% yields in a respective manner.…”

Section: Cà H Functionalization Of Non-aromatic Heterocyclesmentioning

confidence: 99%

Late‐Stage Alkylation of Heterocycles Using N‐(Acyloxy)phthalimides

Parida

Hota

Kumar

et al. 2021

Chemistry An Asian Journal

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Synthetic methods enabling late-stage modification of heterocycles hold tremendous importance in the pharmaceutical and agrochemical industry and drug discovery. Accordingly, efficient, functional group tolerant and selective late-stage alkylation of valuable molecular entities is of enormous significance and well-acknowledged in medicinal chemistry. Radical alkylation of heteroarenes employing carboxylic acids as the alkyl radical precursor represents one of the most direct ways of CÀ H functionalizations of heterocycles. Recently, the field has undergone a revolutionary development especially with regard to the generation of alkyl radicals under much milder conditions. In this regard N-(acyloxy)phthalimides (NHPI esters) have emerged as a suitable precursor of a diverse set of alkyl radicals allowing formal CÀ H alkylation of not only N-heteroarenes but a diverse set of non-aromatic heterocycles under visible light photocatalysis or electrochemical conditions. This review delineates all these discoveries and provides readers a comprehensive overview of this rapidly expanding field.

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“…First, the research group of Dong and Zhou designed a Nhydroxyphthalimide (NHPI) ester as the synthetic equivalent of an aliphatic C-centered radical. [19] Indeed, using these carboxylic acid derivatives in combination with Ru(bpy) 3 Cl 2 [20] and DABCO under sun-light, they could obtain a small collection of C-3 alkylated quinoxalin-2-ones among other related heterocycles such as coumarins, quinolones and chromenones (Scheme 1). The corresponding quinoxalin-2-ones bearing alkyl and cycloalkyl residues were obtained in moderate yields (61-74 %).…”

Section: Introductionmentioning

confidence: 99%