Boron is a cornerstone element within synthetic chemistry. Classically, organoboron reagents have been used as non-toxic and bench-stable nucleophiles in numerous catalytic methodologies, in particular transition metal-based cross-coupling reactions (e.g., Suzuki-Miyaura 1,2 , Chan-Lam, and Hayashi reactions). Further applications are broad ranging including within photocatalysis and materials chemistry; however, the rise of boron in pharmaceutical design is of particular significance. Heteroatoms are prolific in drug discovery with nitrogen, oxygen, and fluorine especially prevalent. Borylated heterocycles are becoming key warheads for pharmaceutical development. The first boron-containing drug approved by the FDA was bortezomib (Figure ), a treatment for multiple myeloma and the first proteasome inhibitor approved for human use. This was followed by tavaborole (Figure ), a topical antifungal. Structurally, tavaborole is an example of a benzoxaboraheterocycle (BOB). This motif has important properties that offer unique advantages in drug design (Figure ): (1) the vacant p-orbital at boron allows for dynamic covalent binding to nucleophiles, for example, to serine residues in serine proteases. (2) They are isolobal to carboxylic acids whilst having a higher pKa, which can enhance protein binding. (3) Further heteroatoms can be incorporated into the boraheterocycle to influence overall properties and reactivity (e.g., hydrolysis rate, pKa, catalytic activity). These attributes have led to new boron-containing drugs (e.g., xeruborbactam, taniborbactam; Figure ); however, despite increasing in frequency in drug design, the synthesis of BOB scaffolds remains challenging.