The Suzuki–Miyaura coupling has become one of the most important and prevalent methods for the construction of carbon–carbon bonds. Although palladium catalysis has historically dominated the field, the use of nickel catalysis has become increasingly widespread due to its unique ability to cleave carbon–heteroatom bonds that are unreactive toward other transition metals. This presentation will discuss the first nickel-catalyzed Suzuki–Miyaura coupling of amides, which proceeds by an uncommon cleavage of the amide C–N bond following <i>N</i>-Boc activation. The methodology is mild, functional group tolerant, and can be strategically employed in sequential transition metal-catalyzed cross-coupling sequences to unite heterocyclic fragments. These studies demonstrate that amides, despite classically being considered inert substrates, can in fact be harnessed as synthons for use in C–C bond forming reactions through cleavage of the C–N bond using non-precious metal catalysis.

Nickel-catalyzed Suzuki-Miyaura coupling of amides

251st National Meeting (2016)

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