Organoboron species are useful building blocks for pharmaceuticals, materials, and other valuable compounds. Such molecules serve as starting materials for a wide array of synthetic transformations. In particular, the Suzuki-Miyuara coupling of boronic acids or esters with alkenyl or aryl halides and their triflates is a well-established, mild, and versatile method for constructing C�C bonds. The aryl boronic acids and esters used in these reactions are usually prepared from the corresponding aryl halide. Such a reliance on halogenated starting materials was first eased in 1999 by the invention of a thermal, catalytic arene C�H activation/borylation reaction. Shortly thereafter we entered into a collaboration that has led to the development of novel organic transformations utilizing Ir-catalyzed borylations. These reactions are high yielding, functional group tolerant (alkyl, halo-, carboxy, alkoxy-, and protected amino), efficient, and uniquely regioselective. In brief, catalytic C�H activation/borylations allow for the direct construction of aryl boronic esters from hydrocarbon feed stocks in a single step, avoiding aryl halides. Just as significantly, the reactions are inherently clean as they can often be run without solvent and occur with H₂ as the only stoichiometric byproduct. Lastly, once the boronic esters are formed they can be cross-coupled without isolation. Recent advances and applications of this chemistry will be presented.