With regards to the coupling of aryl bromides and electron rich aryl iodides, the low coupling efficiency often observed could be overcome by controlling the RAE consumption rate through its slow addition (condition B, Figure ). Under these mildly reductive conditions, oxidatively sensitive motifs like thiophene (41), 9H-carbazole (42), benzo[d]thiazole (43), aniline (44), and even free phenol functionalities (47) are tolerated. This slow addition protocol could be used to engage previously problematic substrates. Whereas Boc-protected indazole 37 had poor coupling efficiency under condition A (<5% yield), using condition B the yield became synthetically useful (58% yield). These same conditions could be applied to decarboxylative alkenylation using alkenyl bromides (Figure ).