Abstract
A mild, efficient and regioselective method for para‐amination of activated arenes has been developed through a combination of iron and copper catalysis. A diverse range of products were obtained from an operationally simple one‐pot, two‐step procedure involving bromination of the aryl substrate with the powerful Lewis acid iron(III) triflimide, followed by a copper(I)‐catalysed N‐arylation reaction. This two‐step dehydrogenative process for the regioselective coupling of aromatic C−H bonds with non‐activated amines was applicable to anisole‐, phenol‐, aniline‐ and acetanilide‐type aryl compounds. Importantly, the arene substrates were used as the limiting reagent and required no protecting‐group manipulations during the transformation.
Highlights
A mild, efficient and regioselective method for para-amination of activated arenes has been developed through a combination of iron and copper catalysis
Aryl amination was conducted by nitration of the aromatic ring, followed by reduction but the use of strongly acidic conditions has limited the general application of this method.[2]
Recently has a directed meta-amination process been reported[8] and only a few examples are known for directed para-amination utilising transition-metal, organo- or photocatalysis, as well as non-catalytic oxidative methods.[9]
Summary
A mild, efficient and regioselective method for para-amination of activated arenes has been developed through a combination of iron and copper catalysis. We report a one-pot, two-step method for the coupling of aryl CÀH bonds with NÀ H bonds by using a combination of iron(III)- and copper(I)-catalysis (Figure 1 c).
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