Palladium-Catalyzed Regio- and Stereoselective C–H Alkynylation of Conjugated Dienols

The regioselective activation of alkenyl C-H bonds in conjugated dienols presents significant challenges due to the presence of multiple similarly reactive sites. In this study, we developed a palladium-catalyzed alkynylation method that is both regio- and stereoselective for the activation of internal alkenyl C-H bonds. This approach provides an efficient and versatile strategy for synthesizing dienyne derivatives with precise <i>Z</i> and <i>E</i> configurations. Stereocontrol is achieved through the introduction of acetate salts, which effectively modulate the reaction pathway, allowing for selective outcomes via either a C-H activation process or a Heck coupling mechanism. This innovative strategy not only enhances the specificity of the synthesis but also broadens the potential applications of the resulting dienyne derivatives in various fields.

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Publication Details

Journal
JACS Au
Published
2025-11-24
DOI
https://doi.org/10.1021/jacsau.5c01417
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Palladium-Catalyzed Regio- and Stereoselective C–H Alkynylation of Conjugated Dienols

Yun‐He Xu, Meng‐Wei Yang, Huan-Xuan Lu, Junwei Zhang
JACS Au
Catalytic C–H Functionalization Methods
article

Palladium-Catalyzed Regio- and Stereoselective C–H Alkynylation of Conjugated Dienols

Yun‐He Xu, Meng‐Wei Yang, Huan-Xuan Lu, Junwei Zhang
article en

Abstract

The regioselective activation of alkenyl C-H bonds in conjugated dienols presents significant challenges due to the presence of multiple similarly reactive sites. In this study, we developed a palladium-catalyzed alkynylation method that is both regio- and stereoselective for the activation of internal alkenyl C-H bonds. This approach provides an efficient and versatile strategy for synthesizing dienyne derivatives with precise <i>Z</i> and <i>E</i> configurations. Stereocontrol is achieved through the introduction of acetate salts, which effectively modulate the reaction pathway, allowing for selective outcomes via either a C-H activation process or a Heck coupling mechanism. This innovative strategy not only enhances the specificity of the synthesis but also broadens the potential applications of the resulting dienyne derivatives in various fields.

JACS AuVol. 5(12)
University of Science and Technology of China (CN)
Openalex Percentile: Top 73%
Catalytic C–H Functionalization Methods
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