Based on our preliminary observations of the impact of the electronics of the substituent, increasing electron density (oxadiazole relative to ester) results in a bathochromic shift in the fluorescence emission. Therefore, we hypothesized that phenyl-substituted borindolizines would afford further redshifted fluorophores. To access the required pyridyl phenyl precursors, we employed a Barluenga-Valdés cross-coupling between pyridotriazoles and aryl boronic acids as demonstrated by Shen and coworkers (see Supporting Information). Employing the standard heterocycle forming conditions, the scope of pyridyl phenyls with varying electronics were reacted to form green-emissive borindolizines 3h -3n in moderate to good yields (λmax,em of 483-519 nm). Gratifyingly, 2-bromo substituted (3n) and 4-chloro substituted (3j) borindolizines could be deprotonated by n-butyllithium and borylated in appreciable yields with no observable amounts of dehalogenation products.