Synthesis of <i>C</i>‐Aryl Glycosides via Ru‐Catalyzed Remote C−H Glycosylation of 8‐Aminoquinoline Amides

Shi, Wei‐Yu; Li, Hu-Yi; Gou, Xue‐Ya; Luan, Yu‐Yong; Zheng, Nian; Zhang, Zhe; Niu, Zhi-Jie; Liu, Xue-Yuan; Liang, Yong‐Min

doi:10.1002/adsc.202200549

Cited by 7 publications

(1 citation statement)

References 49 publications

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“…resulted in a product showing H/D exchange at the ortho positions (Scheme 3C), which suggests that this reaction might involve a reversible C−H activation process. Based on our experimental results and previous reports, 11 we propose that these C5−selective C−H aryl etherification reactions of 8-amidoquinolines proceed via the mechanism shown in Scheme 4. First, 8-amidoquinoline 1 and Pd(II) catalyst I combine by means of proton abstraction to generate complex II, which undergoes intramolecular metallization to afford complex III.…”

supporting

confidence: 72%

Palladium-Catalyzed Coordination-Induced Remote C–H Aryl Etherification/Amination of 8-Amidoquinolines

Xun,

Wang,

Song

et al. 2024

Org. Lett.

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Herein, we report a direct method for palladium-catalyzed coordination-induced oxidative remote C−H aryl etherification of 8-amidoquinolines with p-benzoquinone monoacetal. The method provides access to C5-aryl etherified quinolines and shows site-selectivity different from that of typical palladium-catalyzed C(sp 2 )−H activation reactions. The p-benzoquinone monoacetals act both as oxidants and as aryl etherification reagents. By using proper substrates, C5-aminated quinolines and C4etherifed 1-naphthylamine could also be formed.

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supporting

confidence: 72%

Palladium-Catalyzed Coordination-Induced Remote C–H Aryl Etherification/Amination of 8-Amidoquinolines

Xun,

Wang,

Song

et al. 2024

Org. Lett.

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Synthesis of C‐Aryl Glycosides by C−H Functionalization

Gou

Zhu

Zhang

et al. 2023

Chemistry A European J

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In recent years, the synthesis of C‐aryl glycosides hrough C−H functionalization has attracted extensive attention of organic synthesis chemists due to its steps and atomic economy. In this concept, we systematically summarizes the synthesis of C‐aryl glycosides with diverse regioselectivity and diastereoselectivity from the perspective of C−H arylation of glycosides and C−H glycosylation of arenes. It can be found that a series of recently developed C−H glycosylation reactions have higher site‐selectivity and diastereomeric selectivity than Friedel–Crafts glycosylation reaction. The reaction conditions are milder, which can be compatible with acid‐sensitive protective groups, such as acetals or ketals, and the deprotection is more convenient. It can be seen that there are few reports on remote C−H glycosylation of aromatic hydrocarbons, which is a new field and needs further research. In addition, C−H glycosylation has a lot of shortcomings, which need to be further explored: a) the precise regulation of stereoselectivity in the reaction process also needs further optimization; b) the research on the reaction mechanism is almost limited to DFT calculation, and there is no exact experimental evidence. For key parts, such as the specific reaction mechanism between cyclo‐metal intermediates and glycosyl donors in ortho‐CAr−H glycosylation is still unclear; c) due to the fact that aryl glycoside compounds contain bare hydroxyl groups in practical applications, it is an urgent problem to realize the compatibility of glycoside substrates containing naked hydroxyl groups or to remove the protective groups on hydroxyl groups by a mild and efficient method after the reaction; d) In this rapidly developing field, we need to study a greener, more economical and more practical C−H glycosylation of arenes in the future, which will be conducive to the synthesis of C‐aryl glycosides with more biological application significance.

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Six-membered ring systems: pyridines and benzo derivatives

Badenock

2023

Progress in Heterocyclic Chemistry

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Synthesis of C‐Aryl Glycosides via Ru‐Catalyzed Remote C−H Glycosylation of 8‐Aminoquinoline Amides

Cited by 7 publications

References 49 publications

Palladium-Catalyzed Coordination-Induced Remote C–H Aryl Etherification/Amination of 8-Amidoquinolines

Palladium-Catalyzed Coordination-Induced Remote C–H Aryl Etherification/Amination of 8-Amidoquinolines

Synthesis of C‐Aryl Glycosides by C−H Functionalization

Six-membered ring systems: pyridines and benzo derivatives

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