Palladium-catalyzed distal γ- and ε-benzylation, allylation and allenylation of enones

We report herein a palladium-catalyzed distal alkylation of silyldienol and silyltrienol ethers of enones through coupling with activated halides to achieve new <i>endo</i>- and <i>exo</i>-alkylated motifs. Additionally, by employing propargyl bromides, synthetically useful linear allenes along with functionalized enones have been synthesized. Low-catalyst loading, and late-stage transformations of pharmaceutically relevant molecules further showcase the importance of the present protocol.

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Publication Details

Journal
Chemical Communications
Published
2024-12-30
DOI
https://doi.org/10.1039/d4cc05607h
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Palladium-catalyzed distal γ- and ε-benzylation, allylation and allenylation of enones

Manmohan Kapur, Pooja Sah
Chemical Communications
Catalytic C–H Functionalization Methods
article

Palladium-catalyzed distal γ- and ε-benzylation, allylation and allenylation of enones

Manmohan Kapur, Pooja Sah
article en

Abstract

We report herein a palladium-catalyzed distal alkylation of silyldienol and silyltrienol ethers of enones through coupling with activated halides to achieve new <i>endo</i>- and <i>exo</i>-alkylated motifs. Additionally, by employing propargyl bromides, synthetically useful linear allenes along with functionalized enones have been synthesized. Low-catalyst loading, and late-stage transformations of pharmaceutically relevant molecules further showcase the importance of the present protocol.

Chemical CommunicationsVol. 61(9)
Indian Institute of Science Education and Research, Bhopal (IN)
Openalex Percentile: Top 82%
Catalytic C–H Functionalization Methods
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