Antimicrobial resistance represents one of the greatest threats to modern medicine’s success with repercussions impacting nearly all specialties. While addressing this issue requires expertise from multiple fields, the ability to continuously generate new antibiotics represents an integral piece of any concrete and lasting solution. In recent years this pipeline has largely stagnated, leaving a large gap in antibiotic research. Due to the presence of a double membrane envelope, Gram-negative bacteria present a unique and urgent challenge as their physiology makes them especially effective at evading current bactericidal agents. Recently, the lipoprotein trafficking complex, LolCDE, has been identified as a potential target of future antibiotics. LolCDE, and associated proteins LolA and LolB, facilitate the localization of lipoproteins from the inner membrane across the periplasm and into the outer membrane. This process is essential for bacterial survival and inhibition results in cell death. A team of researchers at AstraZeneca identified the imidazole derivative 2as a relatively potent inhibitor of LolCDE, synthesizing the compound via a sequential Suzuki coupling starting with a dibrominated precursor. This degree project identifies the SEM-switch method as a more reliable and efficient strategy for imidazole functionalization and demonstrates its application to the creation of a series of 2 analogues.