[open to air] (1.5 equiv.) Higher order heterocycles that bear fused aromatic rings are important subclasses of arenes as well. Unprotected indole motifs were well tolerated in this reaction as 5iodoindole was coupled efficiently to afford 28 in 61% yield while giving a modest 33% conversion with the corresponding bromide. Quinoline, another important bicycle which is usually functionalized via Minisci approaches, could be coupled to the free alkyne bearing RAE to give 29 in 42% yield from the iodo-quinoline and 12% from the bromide. Pyrazolopyrimidine derivate 30 was successfully accessed in 31% yield from the corresponding bromide. Prior published routes to 30 involved the coupling of an alkyl bromide in a reductive cross electrophile coupling mediated by zinc in 15% yield. Finally, sulfonamide-protected azaindole-containing cyclobutanone 31 was synthesized in 34% yield with this cross-coupling protocol while only the previously reported electrochemical approach gave comparable yields.