Visible light-promoted, photocatalyst-free decarboxylative alkylation of 2<i>H</i>-indazoles <i>via</i> electron donor–acceptor complex activation

Wang, Jin; Song, Qingyuan; He, Xing; Ma, Chunhua; Jiang, Yuqin; Fan, Jing

doi:10.1039/d2nj02766f

Cited by 3 publications

(1 citation statement)

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“…The findings of this study significantly expanded the synthetic toolbox for accessing functionalized coumarin derivatives and related nitrogen-containing heterocycles, opening up exciting possibilities for their diverse applications in other fields. Similarly, the regioselective photodecarboxylative C–H alkylation of 2 H -indazoles and azauracils using NaI/PPh 3 as mediators and redox esters 3 was reported by the research groups of Murarka [ 18 ] and Fan [ 19 ], respectively.…”

Section: Reviewmentioning

confidence: 72%

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

Liu,

Zhou,

Tang

et al. 2023

Beilstein J. Org. Chem.

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Photoredox catalysis plays a crucial role in contemporary synthetic organic chemistry. Since the groundbreaking work of Shang and Fu on photocatalytic decarboxylative alkylations in 2019, a wide range of organic transformations, such as alkylation, alkenylation, cyclization, amination, iodination, and monofluoromethylation, have been progressively achieved using a combination of iodide and PPh3. In this review, we primarily focus on summarizing the recent advancements in inexpensive and readily available iodide/phosphine-mediated photoredox radical transformations.

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Section: Reviewmentioning

confidence: 72%

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

Liu,

Zhou,

Tang

et al. 2023

Beilstein J. Org. Chem.

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C−H Functionalization of Heteroarenes via Electron Donor‐Acceptor Complex Photoactivation

Mondal,

Ghosh,

Lai

et al. 2024

ChemSusChem

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C─H Functionalization of heteroarenes stands as a potent instrument in organic synthesis, and with the incorporation of visible light, it emerged as a transformative game‐changer. In this domain, electron donor‐acceptor (EDA) complex, formed through the pairing of an electron‐rich substrate with an electron‐accepting molecule, has garnered substantial consideration in recent years due to the related avoidance of the requirement of photocatalyst as well as oxidant. EDA complexes can undergo photoactivation under mild conditions and exhibit high functional group tolerance, making them potentially suitable for the functionalization of biologically relevant heteroarenes. This review article provides an overview of recent advancements in the field of C─H functionalization of heteroarenes via EDA complex photoactivation with literature coverage up to April, 2024.

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Five-membered ring systems: with more than one N atom

Yet

2023

Progress in Heterocyclic Chemistry

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Visible light-promoted, photocatalyst-free decarboxylative alkylation of 2H-indazoles via electron donor–acceptor complex activation

Abstract: A transition-metal-free and traditional dye-free visible light-driven directly alkylation of 2-aryl-2H-indazoles was developed in the catalytic of an electron donor-acceptor (EDA) complex among alkyl N-hydroxyphthalimide (NHPI) esters, triphenylphosphine (PPh3), and...

Cited by 3 publications

References 39 publications

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

C−H Functionalization of Heteroarenes via Electron Donor‐Acceptor Complex Photoactivation

Five-membered ring systems: with more than one N atom

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