Intermolecular Carbopalladation of Arynes

The aryne C—C triple bond is highly reactive toward palladation processes, and the initially formed arylpalladium intermediate can undergo a variety of transformations with an appropriate reagent in an intermolecular, giving rise to 1,2-functionalized benzene derivatives, or in an intramolecular manner, leading to benzo-fused (hetero)carbocyclic systems. 

SCHEME 12.56 Combined Pd-catalyzed strategies initiated by carbopalladation of arynes. 

6 Catalytic Insertion Reactions of Arynes into r-Bonds 

Yoshida, Kunai et al. have reported some reactions of this type, complementing the transition metal-free aryne insertion into o-bonds. Mechanistically, these reactions could proceed via carbopalladation of arynes by the palladium complex arising from the initial oxidative 

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