Palladium-Catalyzed Cross-Coupling of Aryl Bromides and Chlorides with Trimethylsilylalkynes under Mild Conditions

Herein, we disclose a palladium-catalyzed cross-coupling of aryl bromides and chlorides with trimethylsilylalkynes under mild reaction conditions. This method utilizes commercially available and air stable palladium precatalysts and avoids the use of copper cocatalysts. Moreover, it allows for the synthesis of a wide range of disubstituted alkynes in high yields with excellent functional group tolerance. The utility of the developed method was further demonstrated via the late-stage alkynylation of pharmaceuticals and natural bioactive compounds.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-09-02
DOI
https://doi.org/10.1021/acs.joc.4c01499
Citations
2
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
0.50
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article

Palladium-Catalyzed Cross-Coupling of Aryl Bromides and Chlorides with Trimethylsilylalkynes under Mild Conditions

Girish C. Sati, Adrián Tlahuext-Aca, Yang Gao, Quyen Nguyen et al.
2 citations
The Journal of Organic Chemistry
Catalytic Cross-Coupling Reactions
0.50
article

Palladium-Catalyzed Cross-Coupling of Aryl Bromides and Chlorides with Trimethylsilylalkynes under Mild Conditions

Girish C. Sati, Adrián Tlahuext-Aca, Yang Gao, Quyen Nguyen, Daniel Valco, Jinpeng Zhao
article en
2 citations

Abstract

Herein, we disclose a palladium-catalyzed cross-coupling of aryl bromides and chlorides with trimethylsilylalkynes under mild reaction conditions. This method utilizes commercially available and air stable palladium precatalysts and avoids the use of copper cocatalysts. Moreover, it allows for the synthesis of a wide range of disubstituted alkynes in high yields with excellent functional group tolerance. The utility of the developed method was further demonstrated via the late-stage alkynylation of pharmaceuticals and natural bioactive compounds.

The Journal of Organic ChemistryVol. 89(18)
Corteva (United States) (US)
Clean water and sanitation
Openalex Percentile: Top 40%
Catalytic Cross-Coupling Reactions
0.50
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Palladium-Catalyzed Cross-Coupling of Aryl Bromides and Chlorides with Trimethylsilylalkynes under Mild Conditions — Girish C. Sati, Adrián Tlahuext-Aca, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS