The current utility and future potential of multiborylated alkanes

Organoboron chemistry has become a cornerstone of modern synthetic methodology. Most of these reactions use an organoboron starting material that contains just one C(sp2)–B or C(sp3)–B bond; however, there has been a recent and accelerating trend to prepare multiborylated alkanes that possess two or more C(sp3)–B bonds. This is despite a lack of general reactivity, meaning many of these compounds currently offer limited downstream synthetic value. This Review summarizes recent advances in the exploration of multiborylated alkanes, including a discussion on how these products may be elaborated in further synthetic manipulations. Monoborylated alkanes display diverse reactivity and broad application; however, despite an increasing number of approaches to access them, multiborylated alkanes have yet to realize their synthetic potential. This Review highlights the current state-of-the-art in approaches to and synthetic applications of multiborylated alkanes.