2-
or 4-Pyridyl benzylic amines represent a privileged motif in
drug discovery. However, the formation of heterocyclic benzylic amines
with fully substituted α-carbons can require the execution of
lengthy synthetic routes, which limit their application. Addition
of various nucleophilic agents to Ellman’s imines has been
well established; however, there is no precedented literature reported
for pyridyl-type nucleophiles, which are very important for medicinal
chemistry. In this letter, we disclose the development of a one-step
synthesis of heterocyclic benzylic amines with fully substituted α-carbons
from heteroaryl halides and sulfinyl imines. Starting from 2,4-dibromopyridine,
regioselective synthesis of 2- or 4-pyridyl benzylic amines could
be achieved by choosing toluene or MTBE as a solvent.