Nickel- or Palladium-Catalyzed Decarbonylative Transformations of Acyl Halides

Carboxylic acid derivatives such as acyl halides, acid anhydrides, esters, and amides have garnered significant attention as electrophilic coupling partners due to their low cost and ready availability. These derivatives offer distinct advantages in transition-metal-catalyzed decarbonylative transformations for the following reasons: 1) Unlike conventional aryl halides, carboxylic acid derivatives can be readily prepared from carboxylic acids in a single step, making them both economical and synthetically accessible; 2) The leaving group (X) can coordinate with the transition metal center, reducing the energy barrier for the rate-limiting step and other key reaction processes; and 3) When X is basic, cross-coupling reactions can proceed under base-free conditions. Since acyl chlorides are chemically unstable and esters and amides exhibit low reactivity, we have recently focused on acyl fluorides, which provide an optimal balance between stability and reactivity. In recent years, we have successfully developed a series of nickel- or palladium-catalyzed decarbonylative protocols, enabling efficient methodologies for constructing carbon-carbon, carbon-heteroatom, and carbon-halogen bonds. This systematic work broadens the scope of synthetic organic chemistry and catalysis, laying a strong foundation for future advancements in the field.