Palladium(II)-Catalyzed Norbornene-Mediated Selective <i>meta</i>-C–H Silylation for the Synthesis of Arylsilanes from Primary Benzamides

Li, Wenguang; Shi, Shukui; Cao, Man; Gao, Wenchao; Zhang, Xu; Li, Wentao; Yu, Yongqi; Li, Ting

doi:10.1021/acs.orglett.4c01841

Org. Lett.

2024

DOI: 10.1021/acs.orglett.4c01841

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Palladium(II)-Catalyzed Norbornene-Mediated Selective meta-C–H Silylation for the Synthesis of Arylsilanes from Primary Benzamides

Wenguang Li,

Shukui Shi,

Man Cao

et al.

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Cited by 3 publications

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Visible‐Light‐Induced C−H Silylation of Azauracils with Hydrosilanes

Yu,

You,

et al. 2024

Adv Synth Catal

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A C–H silylation of azauracils was developed via the combination of organic photoredox and hydrogen atom transfer (HAT) catalysis. Using 1,2,3,5‐tetrakis(carbazol‐9‐yl)‐4,6‐dicyanobenzene (4CzIPN) as the photocatalyst, quinuclidine as the HAT catalyst, and silanes as the silyl radical sources, a variety of silylated azauracils were synthesized in 43‐87% yields. Moreover, pyrazinone, cinnolinone, and chromone were also compatible with this catalytic system. The reaction is suitable for late‐stage functionalization of drugs and complex molecules, and the transformation can be easily scaled up to the gram level. Mechanistic studies suggest that the silylation reaction is likely to proceed through a radical mechanism.

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Visible‐Light‐Induced C−H Silylation of Azauracils with Hydrosilanes

Yu,

You,

et al. 2024

Adv Synth Catal

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Palladium/norbornene-catalyzed C–H/N–H cycloaddition of carbazoles with 2-halobenzoic acid derivatives

Liu,

Nan,

et al. 2024

Chem. Commun.

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Palladium-catalyzed annulation and intermolecular hydroamination involving norbornene derivatives: synthesis of indanones and N-alkylamines

Li,

Cheng,

Cao

et al. 2024

Chem. Commun.

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Palladium(II)-Catalyzed Norbornene-Mediated Selective meta-C–H Silylation for the Synthesis of Arylsilanes from Primary Benzamides

Cited by 3 publications

References 65 publications

Visible‐Light‐Induced C−H Silylation of Azauracils with Hydrosilanes

Visible‐Light‐Induced C−H Silylation of Azauracils with Hydrosilanes

Palladium/norbornene-catalyzed C–H/N–H cycloaddition of carbazoles with 2-halobenzoic acid derivatives

Palladium-catalyzed annulation and intermolecular hydroamination involving norbornene derivatives: synthesis of indanones and N-alkylamines

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