Abstract
Herein we report a study on the reactivity of C2‐quinoline‐substituted furan, thiophene and pyrrole derivatives in palladium‐catalyzed direct C–H arylation. The regioselectivity of the reaction was strongly influenced by site position of the attached five‐membered heterocycle thus giving rise to C3‐ and/or C5‐arylated products. Furthermore, the Hammett correlation performed on 5‐substituted‐8‐(furan‐2‐yl)quinolines indicates that a marginally positive charge is building up in the rate determining transition state and thus pointing towards the electrophilic metalation‐deprotonation reaction mechanism.
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