Safe handling of boranes at scale

The safe handling of borane complexes and alkylboranes (trialkylboranes, dialkylboranes, and trialkylborohydride reagents) and related workup issues are addressed. Oxidation of alkylboranes and quenching of reaction mixtures to safely decompose the reagent or products are discussed. Several case studies demonstrate large-scale applications of borane reagents for carboxylic acid reduction, reductive amination, and hydroboration followed by oxidation.