Environmental concerns and a rising focus on sustainability are of increasing importance in society. As these concerns begin to impose limitations on synthetic chemistry and industrially relevant processes, more efficient alternatives to facilitate the synthesis of organic compounds must be developed. As one of the Twelve Principles of Green Chemistry, catalysis will be a vital technology to both society and the chemical industry. The use of cooperative catalysts, activation by light (photocatalysis), and electrical current (electrochemistry) has led to new processes of chemical bond formation, as well as expansion of the scope of previously explored methodologies. However, even with these new catalytic strategies, the use of the common hydroxyl functional remains under-explored. In this regard, boronic acids have recently emerged as catalysts for their mild and selective activation. Herein, the development of three boronic acid catalysed methodologies will be discussed. Chapter two will focus on the development of a boronic acid catalysed coupling of π-activated alcohols with borate and silane nucleophiles. In a direct comparison between potassium trifluoroborates and organosilane nucleophiles, organosilanes lead to higher reaction yields, a wider substrate scope, and proceed with high E/Z selectivity when alkenyl silanes are employed as substrates. Furthermore, the reaction proceeds under mild conditions with up to near quantitative. This method complements existing methodologies as a unifying strategy for deoxygenative coupling reactions of alcohols with pseudo-organometallic reagents. Given the well explored reactivity and value azides and nitriles possess as precursors to a variety of nitrogenous compounds, the ACS Green Institute Pharmaceutical Roundtable has ranked their preparation, without the use of metal salts, as a critical area of research. Chapter three will discuss the preparation of azides and nitriles using bench-stable azidotrimethylsilane and trimethylsilyl cyanide. Azidotrimethylsilane and trimethylsilyl cyanide are silane-bound, nucleophilic reagents capable of intercepting a presumed generated carbocation. A variety of diarylaceto nitriles, diarylmethyleneazides, and otherwise difficult to prepare allylic azides, are reported in modest to near quantitative yields. Due to the importance that α-functionalized saturated N- and O- heterocycles have in medicinal chemistry, novel strategies for their preparation are of high value. Chapter 4 will discuss the initial results of a boronic acid catalysed coupling of cyclic hemiaminals and cyclic hemiacetals with silane nucleophiles. Previous studies have highlighted various Lewis and Brønsted acids that are capable of catalytically activating cyclic hemiacetals for nucleophilic substitution. However, this is the first report on the use of cyclic hemiaminals as substrates. Initial results suggest compatibility of a diverse scope of organosilane nucleophiles and N-protecting groups. Moreover, the optimized methodology proceeds under mild conditions, while producing only environmentally benign by-products.