The oxidative α-functionalization of 2-aryl-1,2,3,4-tetrahydroisoquinolines
(THIQs) promoted by a versatile heterogeneous nanocatalyst consisting
of copper nanoparticles immobilized on silica-coated maghemite (CuNPs/MagSilica)
has been accomplished. The methodology was successfully applied in
the cross-dehydrogenative coupling (CDC) reaction of N-aryl THIQs and other tertiary amines with nitromethane as a pro-nucleophile
(aza-Henry reaction) and the α-oxidation of THIQs with O2 as a green oxidant. Phosphite, alkyne, or indole derivatives
were also shown to be suitable candidates for their use as pro-nucleophiles
in the CDC reaction with THIQs. The catalyst, with very low copper
loading (0.4–1.0 mol % Cu), could be easily recovered by means
of an external magnet and reused in four cycles without significant
loss of activity.
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