Despite their prevalence in medicine and materials, the installation of heteroaromatic moieties persists as a challenge in the syntheses of small molecules. While many high-throughput experimentation adaptations exist for common cross-coupling reactions, available options for C(sp2)–C(sp3) and C(sp2)–C(sp2) cross-electrophile couplings have remained underdeveloped. Using recent technological advancements to circumvent the operational challenges inherent to heterogeneous reactions, the engagement of commercially abundant and conventionally challenging heteroaryl halide electrophiles has been realized. With these strategies, heteroaryl-alkyl and biheteroaryl linkages can be formed with reliably competitive success rates. Subsequent work targets the development of a new Ni-only catalyzed cross-electrophile coupling between aryl bromides and aryl chlorides, with a focus on achieving method generality through mechanistically guided reaction design.
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