Tandem Fe/Zn or Fe/In Catalysis for the Selective Synthesis of Primary and Secondary Amines via Selective Reduction of Primary Amides

Tandem iron/zinc or iron/indium-catalysed reductions of various primary amides to amines under hydrosilylation conditions are reported under visible light activation. By a simple modification of the nature of the co-catalyst (Zn(OTf)(2) vs In(OTf)(3)), Fe(CO)(4)(IMes) can promote the highly chemoselective reduction of primary amides into primary amines (21 examples, up to 93 % isolated yields) and secondary amines (8 examples, up to 51 % isolated yields), respectively. Notably, both benzamide and alkanamide derivatives can be reduced.

Automated summary

This study reports the tandem iron/zinc or iron/indium-catalysed reductions of various primary amides to amines, under visible light activation. These reactions show high chemoselectivity and can convert primary amides into primary and secondary amines.