Challenging Nickel-Catalyzed Amine Arylations

A primary research focus of Professor Mark Stradiotto’s group at Dalhousie University (Halifax, Canada) is on the design and application of new ancillary ligands for use in addressing outstanding reactivity challenges in metal-catalyzed cross-coupling chemistry and beyond. They are particularly interested in the monoarylation of ammonia and related N–H nucleophiles by use of (hetero)aryl (pseudo)halide reaction partners. Until very recently, only copper- and palladium-based catalysts had proven capable of ammonia monoarylation, with each exhibiting important limitations: reactions involving copper are typically limited to activated aryl bromide or iodide electrophiles under forcing reaction conditions. The group turned their focus on the use of nickel-based catalysts now as they represent an attractive alternative to both copper and palladium, given the desirable reactivity properties of nickel in oxidative addition chemistry and its relatively low cost and large abundance (relative to palladium).

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