In previous studies with 1-hydrosilatrane, the direct reductive amination with aryl amines and aldehydes could be readily enabled using acetic acid as the solvent. Hence, we began our investigation using 4-methoxybenzaldehyde, aniline, and 1-allylsilatrane in acetic acid (Table ). This set of conditions did allow for reaction to take place, but initially gave poor conversion (Entry 1). Increasing the temperature to 40 °C resulted in greater yield (entry 2), with further improvements resulting from using 2 equivalents of the aldehyde and 1-allylsilatrane (entry 3). Attempts to manipulate the yield in inert solvents using acid additivesboth Lewis (Entry 4) and Bronsted (Entry 5) -demonstrated limited reactivity. Finally, trifluoracetic acid was used as a stoichiometric agent in ethanol which resulted in the highest yield (entry 6) of the scanned conditions.