Nitrosylation of imidazo[1,2-a]pyridines in metal free system

Hao, Xin‐Qi; Liu, Wenbo; Xiaojing, Shen; Wang, Wei; Liang, Zhikun; Zhu, Xinju; Song, Mao‐Ping

doi:10.1016/j.jscs.2016.02.004

Cited by 4 publications

(2 citation statements)

References 19 publications

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“…Therefore, new methodologies have been developed to overcome these shortcomings. Methods reported by Hajra and co-workers, Wang and co-workers, and Song and co-workers use alkyl nitrite as the nitroso reagent for the C3–H nitrosylation of imidazo[1,2- a ]pyridine derivatives. Notably, despite the high efficiency of these methodologies, they exhibit limited utility due to safety concerns.…”

Section: Introductionmentioning

confidence: 99%

Photocatalyzed C3–H Nitrosylation of Imidazo[1,2-a]pyridine under Continuous Flow and External Photocatalyst-, Oxidant-, and Additive-Free Conditions

Qiao,

Zhao,

Zhu

et al. 2024

J. Org. Chem.

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This study reports a protocol for the highly regioselective photocatalyzed C−H nitrosylation of imidazo[1,2-a]pyridine scaffolds at the C3 position under a combination of visible-light irradiation and continuous flow without any external photocatalyst. This protocol involves mild and safe conditions and shows good tolerance to air and water along with excellent functional group compatibility and site selectivity, generating various 3nitrosoimidazo[1,2-a]pyridines in excellent yields under photocatalyst-, oxidant-, and additive-free conditions.Notably, the proposed nitrosylation reaction, which introduces the chromophore NO into imidazo[1,2-a]pyridine scaffolds, occurs efficiently under visible-light irradiation without any additional photocatalyst owing to the intense light-absorption characteristics of the nitrosylation products. This study could guide future studies on the development of green organic-synthesis strategies with a wide variety of potential applications.

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Section: Introductionmentioning

confidence: 99%

Photocatalyzed C3–H Nitrosylation of Imidazo[1,2-a]pyridine under Continuous Flow and External Photocatalyst-, Oxidant-, and Additive-Free Conditions

Qiao,

Zhao,

Zhu

et al. 2024

J. Org. Chem.

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“…Until now, tremendous efforts have been made to construct C–C, C–S, C–O, C–F, and C–P bonds via direct C3 functionalizations. However, the formation of the C–N bond is less investigated. , Recently, the Gryko group prepared polycyclic imidazopyridines via oxidative intramolecular C–H amination . Subsequently, the Hajra group achieved oxidative C–H amination of imidazopyridines in the presence of (diacetoxy)iodobenzene .…”

Section: Introductionmentioning

confidence: 99%

Copper-Mediated C–H Amination of Imidazopyridines with N-Fluorobenzenesulfonimide

Tian

Cui

et al. 2018

J. Org. Chem.

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A copper-mediated direct C3 amination of imidazopyridines has been disclosed under additive-free conditions in short reaction times. This methodology utilizes commercially available N-fluorobenzenesulfonimide (NFSI) as the amino source, which exhibits broad substrate scope and good functional group tolerance. The obtained C3-aminated imidazopyridines can undergo further desulfonylation transformations. Control experiments suggest that this reaction probably proceeds via a free-radical mechanism. Moreover, NFSI also shows potential application in C–H fluorination of imidazopyridines.

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Iodine-Mediated Difunctionalization of Imidazopyridines with Sodium Sulfinates: Synthesis of Sulfones and Sulfides

et al. 2017

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Novel iodine-induced sulfonylation and sulfenylation of imidazopyridines have been described using sodium sulfinates as the sulfur source. This strategy enables highly selective difunctionalization of imidazo[1,2-a]pyridine to access sulfones and sulfides in good yields. A wide range of substrates and functional groups were well-tolerated under optimized conditions. Moreover, control experiments have been conducted, indicating a radical pathway involved in the reaction mechanisms.

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Nitrosylation of imidazo[1,2-a]pyridines in metal free system

Cited by 4 publications

References 19 publications

Photocatalyzed C3–H Nitrosylation of Imidazo[1,2-a]pyridine under Continuous Flow and External Photocatalyst-, Oxidant-, and Additive-Free Conditions

Photocatalyzed C3–H Nitrosylation of Imidazo[1,2-a]pyridine under Continuous Flow and External Photocatalyst-, Oxidant-, and Additive-Free Conditions

Copper-Mediated C–H Amination of Imidazopyridines with N-Fluorobenzenesulfonimide

Iodine-Mediated Difunctionalization of Imidazopyridines with Sodium Sulfinates: Synthesis of Sulfones and Sulfides

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