Synthesis of Triaryl‐Substituted Acyclic Olefins via Palladium‐Catalyzed γ‐C(sp <sup>3</sup> )‐H Diarylation of 2‐(2‐Phenylpropyl)pyridine Derivatives

Abstract This study presents an efficient method for synthesizing triaryl‐substituted acyclic olefins, employing palladium‐catalyzed diarylation of primary C(sp 3 )─H bonds at the γ‐position of 2‐(2‐phenylpropyl)pyridine derivatives, using halogen‐substituted aryl boronic esters as coupling reagents. Intramolecular β‐hydride elimination plays a key role in facilitating the formation of these compounds. The diarylation reaction proceeds smoothly with high functional group tolerance and good yields, even on a gram scale. Preliminary mechanistic studies suggest that the reaction may proceed through a Pd(II)/Pd(IV) catalytic cycle. This approach offers a novel strategy for the one‐pot synthesis of triaryl‐substituted acyclic olefin derivatives.

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Journal
Asian Journal of Organic Chemistry
Published
2025-08-25
DOI
https://doi.org/10.1002/ajoc.202500564
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Synthesis of Triaryl‐Substituted Acyclic Olefins via Palladium‐Catalyzed γ‐C(sp 3 )‐H Diarylation of 2‐(2‐Phenylpropyl)pyridine Derivatives

H. B. Li, Jun Rong Jiang, Junfeng Wang, Zhijun Guo et al.
Asian Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Synthesis of Triaryl‐Substituted Acyclic Olefins via Palladium‐Catalyzed γ‐C(sp 3 )‐H Diarylation of 2‐(2‐Phenylpropyl)pyridine Derivatives

H. B. Li, Jun Rong Jiang, Junfeng Wang, Zhijun Guo, Jinping Li, Lisheng Wang
article en

Abstract

Abstract This study presents an efficient method for synthesizing triaryl‐substituted acyclic olefins, employing palladium‐catalyzed diarylation of primary C(sp 3 )─H bonds at the γ‐position of 2‐(2‐phenylpropyl)pyridine derivatives, using halogen‐substituted aryl boronic esters as coupling reagents. Intramolecular β‐hydride elimination plays a key role in facilitating the formation of these compounds. The diarylation reaction proceeds smoothly with high functional group tolerance and good yields, even on a gram scale. Preliminary mechanistic studies suggest that the reaction may proceed through a Pd(II)/Pd(IV) catalytic cycle. This approach offers a novel strategy for the one‐pot synthesis of triaryl‐substituted acyclic olefin derivatives.

Asian Journal of Organic ChemistryVol. 14(11)
Guangxi University (CN), Zero to Three (US), Guangxi Academy of Sciences (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 83%
Catalytic C–H Functionalization Methods
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