Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of Aliphatic Amides on the Benchtop.

Milauni M Mehta, Timothy B Boit, Jacob E Dander, Neil K Garg

Organic letters 2020 Jan 03

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Suzuki-Miyaura cross-couplings of amides offer an approach to the synthesis of ketones that avoids the use of basic or pyrophoric nucleophiles. However, these reactions require glovebox manipulations, thus limiting their practicality. We report a benchtop protocol for Suzuki-Miyaura cross-couplings of aliphatic amides that utilizes a paraffin capsule containing a Ni(0) precatalyst and NHC ligand. This methodology is broad in scope, is scalable, and provides a user-friendly approach to convert aliphatic amides to alkyl-aryl ketones.

Citation

Milauni M Mehta, Timothy B Boit, Jacob E Dander, Neil K Garg. Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of Aliphatic Amides on the Benchtop. Organic letters. 2020 Jan 03;22(1):1-5