Palladium-Catalyzed\nDual-Tasked <i>ortho</i>-C–H Borylation of Aryl Iodides

The\nPd-catalyzed <i>ortho</i>-C–H borylation of\naryl iodides has been developed through maleimide-relayed C–H\nactivation. In this reaction, the <i>ipso</i>-positions\nand <i>ortho</i>-C–H bonds of aryl iodides are alkylated\nand borylated, respectively, providing a new strategy for C–H\nborylation. The reaction exhibits a broad substrate scope and represents\na modular synthetic method for functionalized 3-aryl succinimides,\nwhich are essential structural motifs in organic compounds with diverse\nbiological activities. Furthermore, the boronate group can be further\nmanipulated, and the practical utility of the reaction has been demonstrated.\nThis work also introduces a new strategy for <i>ipso</i>, <i>ortho</i>-difunctionalization of aryl halides via\nC–H activation.

Publication Details

Journal
Figshare
Published
2024-12-05
DOI
https://doi.org/10.1021/acs.orglett.4c04218.s001
Primary Topic
Catalytic C–H Functionalization Methods
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article
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article

Palladium-Catalyzed\nDual-Tasked ortho-C–H Borylation of Aryl Iodides

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Catalytic C–H Functionalization Methods
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Palladium-Catalyzed\nDual-Tasked ortho-C–H Borylation of Aryl Iodides

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Abstract

The\nPd-catalyzed <i>ortho</i>-C–H borylation of\naryl iodides has been developed through maleimide-relayed C–H\nactivation. In this reaction, the <i>ipso</i>-positions\nand <i>ortho</i>-C–H bonds of aryl iodides are alkylated\nand borylated, respectively, providing a new strategy for C–H\nborylation. The reaction exhibits a broad substrate scope and represents\na modular synthetic method for functionalized 3-aryl succinimides,\nwhich are essential structural motifs in organic compounds with diverse\nbiological activities. Furthermore, the boronate group can be further\nmanipulated, and the practical utility of the reaction has been demonstrated.\nThis work also introduces a new strategy for <i>ipso</i>, <i>ortho</i>-difunctionalization of aryl halides via\nC–H activation.

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Catalytic C–H Functionalization Methods
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