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 focus on the development of the nickel-catalyzed Suzuki–Miyaura coupling of aliphatic amides derived from aliphatic carboxylic acids. In addition, a mild reduction protocol uncovered during these studies will be described. Lastly, applications and extensions of these methodologies will be disclosed to allow for unconventional synthetic conversions. Collectively, these studies reinforce the notion 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 amide C–N bond using non-precious metal catalysis.

Nickel-catalyzed Suzuki–Miyaura couplings of amides: Scope and applications

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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