Borrowing Hydrogen Amination Reactions: A Complex Analysis of Trends and Correlations of the Various Reaction Parameters

Borrowing hydrogen or the hydrogen autotransfer amination is a powerful approach to create single C–N bonds, starting from stable and readily available substrates: amines and alcohols. It is considered as one of the most atom-efficient and green methods to synthesize complex amines. Herein, we attempted to arrange the array of the existing data in a comprehensive and structured manner and determine correlations between the experimental conditions and catalysis outcome both within different groups of catalysts and between the defined groups using the machine analysis. For each type of N-nucleophiles (aromatic, aliphatic, and heteroaromatic amines, amides), the most efficient working conditions were suggested, including attributing the optimal base and temperature regime for each metal.