Visible-light-mediated metal-free decarboxylative acylation of electron-deficient quinolines using α-ketoacids under ambient air

Zheng, Zhongqi; Wu, Yongdi; Lü, Xiaohong; Zhang, Fanglin; Qi, Mei-Fang; Sun, E; Sun, Bing

doi:10.1016/j.tet.2022.132749

Cited by 4 publications

(2 citation statements)

References 75 publications

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“…Diaryl ketones such as anthrone have also been reported as efficient photocatalysts for the decarboxylative acylation of quinolines with -keto acids and 1 O 2 participation. 69 Similarly, phenanthrenequinone transfers energy to triplet oxygen upon visible light irradiation, producing singlet oxygen. 70 This photoexcited catalyst was also proposed to abstract a hydrogen atom from C(sp 3 )-H donors, and the alkyl radicals were scavenged by quinoxalinones and other azaarenes with final 1 O 2 aromatization.…”

Section: Short Review Synthesis Scheme 19 Examples Illustrating Possi...mentioning

confidence: 99%

Advances in Photoinduced Minisci-like Reactions

Martos,

Bosque,

Gonzalez-Gomez

2024

Synthesis

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The Minisci reaction, which has been around for more than five decades, is still the preferred tool for the straightforward alkylation of basic heteroarenes. The recent developments in photocatalysis have opened novel pathways for radical generation under milder and more sustainable conditions. Implementing this approach into the Minisci reaction has renewed interest in this transformation, which is attractive per se in Medicinal Chemistry. Aspects such as sacrificial oxidants, catalysts, and specific reaction conditions should be carefully examined to evaluate the practicability of the protocol. This short review focuses on recent advances (2020 to February 2024) in photoinduced Minisci-type reactions, emphasizing sustainability.1 Introduction2 Using Noble-Metal-Based Photocatalysts3 Noble-Metal-Free Methods Using Sacrificial Oxidants4 Noble-Metal-Free Methods Without Sacrificial Oxidants5 Conclusions and Perspectives

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Section: Short Review Synthesis Scheme 19 Examples Illustrating Possi...mentioning

confidence: 99%

Advances in Photoinduced Minisci-like Reactions

Martos,

Bosque,

Gonzalez-Gomez

2024

Synthesis

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“…Subsequently, the visible-light-promoted metal-free decarboxylative Minisci-type acylation of electron deficient quinolines 236 was disclosed by Sun et al using ambient air as an oxidant. 97 The reaction employs ambient air as the terminal oxidant and anthrone ( 238 ) as the C–H abstraction organophotoredox catalyst. However, the protocol gave acylated heteroarenes 237 in modest to moderate yields (Scheme 85).…”

Section: Photo(redox)-catalyzed Decarboxylative Transformationsmentioning

confidence: 99%

Recent advances in catalytic decarboxylative transformations of carboxylic acid groups attached to a non-aromatic sp²or sp carbon

Rahaman¹,

Chauhan²,

Bhadra³

2023

Org. Biomol. Chem.

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Visible‐Light‐Driven Synthesis of 6‐Aroyl Benzimidazo[1,2‐c]quinazolines from N‐Cyanobenzimidazoles and α‐Keto Acids by Radical Relay Cyclization

Hu,

Liu,

et al. 2024

Eur J Org Chem

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A diverse array of 6‐aroyl benzimidazo[1,2‐c]quinazolines was successfully synthesized using easily obtainable N‐cyanobenzimidazoles and α‐keto acids, facilitated by photoredox catalysis. A mechanistic investigation revealed that this methodology might involve both photoredox and energy transfer catalytic cycles, generating acyl radicals that subsequently promote radical relay cyclization.

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Visible-light-mediated metal-free decarboxylative acylation of electron-deficient quinolines using α-ketoacids under ambient air

Cited by 4 publications

References 75 publications

Advances in Photoinduced Minisci-like Reactions

Advances in Photoinduced Minisci-like Reactions

Recent advances in catalytic decarboxylative transformations of carboxylic acid groups attached to a non-aromatic sp²or sp carbon

Visible‐Light‐Driven Synthesis of 6‐Aroyl Benzimidazo[1,2‐c]quinazolines from N‐Cyanobenzimidazoles and α‐Keto Acids by Radical Relay Cyclization

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Visible-light-mediated metal-free decarboxylative acylation of electron-deficient quinolines using α-ketoacids under ambient air

Cited by 4 publications

References 75 publications

Advances in Photoinduced Minisci-like Reactions

Advances in Photoinduced Minisci-like Reactions

Recent advances in catalytic decarboxylative transformations of carboxylic acid groups attached to a non-aromatic sp2or sp carbon

Visible‐Light‐Driven Synthesis of 6‐Aroyl Benzimidazo[1,2‐c]quinazolines from N‐Cyanobenzimidazoles and α‐Keto Acids by Radical Relay Cyclization

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Recent advances in catalytic decarboxylative transformations of carboxylic acid groups attached to a non-aromatic sp²or sp carbon