Synthesis of Triaryl‐Substituted Acyclic Olefins via Palladium‐Catalyzed γ‐C(sp3)‐H Diarylation of 2‐(2‐Phenylpropyl)pyridine Derivatives

This study presents an efficient method for synthesizing triaryl-substituted acyclic olefins, employing palladium-catalyzed diarylation of primary C(sp³)-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.

Abstract

This study presents an efficient method for synthesizing triaryl-substituted acyclic olefins, employing palladium-catalyzed diarylation of primary C(sp³)─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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