Palladium-Catalyzed\nCascade Distal C–H Methylation\nand Cyclization for the Construction of Spirooxindole Skeletons

Transition metal-catalyzed C–H methylation represents\na\nstraightforward approach for introducing methyl groups into organic\nmolecules. Herein, we report a palladium-catalyzed alkene-relayed\nremote C–H methylation reaction that utilizes dimethyl carbonate\nas the methylation reagent. The aryl groups distal to a bromo group\nwere dimethylated via C–H activation, leading to the formation\nof spirooxindoles as the final products through C(sp<sup>3</sup>)–H\nactivation and C(sp<sup>3</sup>)–C(sp<sup>3</sup>) coupling.\nThis cascade process involves the formation of four C–C bonds\nand the activation of three C–H bonds. The reaction not only\nprovides a new approach to C–H methylation but also offers\na novel method for constructing spirooxindole skeletons by merging\nskeleton construction and methylation into a single step.

Publication Details

Journal
Figshare
Published
2024-10-18
DOI
https://doi.org/10.1021/acs.orglett.4c03315.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Palladium-Catalyzed\nCascade Distal C–H Methylation\nand Cyclization for the Construction of Spirooxindole Skeletons

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Catalytic C–H Functionalization Methods
article

Palladium-Catalyzed\nCascade Distal C–H Methylation\nand Cyclization for the Construction of Spirooxindole Skeletons

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Abstract

Transition metal-catalyzed C–H methylation represents\na\nstraightforward approach for introducing methyl groups into organic\nmolecules. Herein, we report a palladium-catalyzed alkene-relayed\nremote C–H methylation reaction that utilizes dimethyl carbonate\nas the methylation reagent. The aryl groups distal to a bromo group\nwere dimethylated via C–H activation, leading to the formation\nof spirooxindoles as the final products through C(sp<sup>3</sup>)–H\nactivation and C(sp<sup>3</sup>)–C(sp<sup>3</sup>) coupling.\nThis cascade process involves the formation of four C–C bonds\nand the activation of three C–H bonds. The reaction not only\nprovides a new approach to C–H methylation but also offers\na novel method for constructing spirooxindole skeletons by merging\nskeleton construction and methylation into a single step.

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Catalytic C–H Functionalization Methods
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