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.