Synthesis ofPolysubstituted Aromatics via the Pd(II)-InitiatedBorono-Catellani Reaction

Herein, we report a novel palladium(II)-initiated borono-Catellani reaction that utilizes widely accessible aryl boronic acids that serve as both the reaction-initiating and -terminating substrates for the first time. The borono-Catellani reaction was facilitated by cooperative catalysis between Pd(OAc)<sub>2</sub> and NBE, with air serving as the oxidizing agent, opening new venues for developing novel Catellani-type reactions. Importantly, this method is compatible with a wide range of substrates, including naphthaleneboronic acid, phenylboric acid derivatives, alkyl iodides, and aryl iodides, under these environmentally friendly and mild reaction conditions, thereby demonstrating versatile functional group compatibility for the synthesis of valuable polysubstituted aromatics.

Publication Details

Journal
Figshare
Published
2025-03-07
DOI
https://doi.org/10.1021/acs.orglett.5c00503.s001
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
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article

Synthesis ofPolysubstituted Aromatics via the Pd(II)-InitiatedBorono-Catellani Reaction

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Catalytic Cross-Coupling Reactions
article

Synthesis ofPolysubstituted Aromatics via the Pd(II)-InitiatedBorono-Catellani Reaction

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Abstract

Herein, we report a novel palladium(II)-initiated borono-Catellani reaction that utilizes widely accessible aryl boronic acids that serve as both the reaction-initiating and -terminating substrates for the first time. The borono-Catellani reaction was facilitated by cooperative catalysis between Pd(OAc)<sub>2</sub> and NBE, with air serving as the oxidizing agent, opening new venues for developing novel Catellani-type reactions. Importantly, this method is compatible with a wide range of substrates, including naphthaleneboronic acid, phenylboric acid derivatives, alkyl iodides, and aryl iodides, under these environmentally friendly and mild reaction conditions, thereby demonstrating versatile functional group compatibility for the synthesis of valuable polysubstituted aromatics.

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Catalytic Cross-Coupling Reactions
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