Nickel-Catalyzed Carbonylation of Secondary Trifluoromethylated, Difluoromethylated, and Nonfluorinated Aliphatic Electrophiles with Arylboronic Acids under 1 atm of CO

The nickel-catalyzed carbonylation of aliphatic electrophiles with the most straightforward CO remains challenging. Here, we describe an example of the nickel-catalyzed carbonylation of secondary alkyl halides with arylboronic acids under 1 atm of CO. The reaction exhibits high functional group tolerance and a broad substrate scope, including trifluoromethylated, difluoromethylated, and difluoroacetylated secondary alkyl iodides and secondary benzyl bromides, providing a general and cost-efficient method to access alkyl ketones, especially alpha-trifluoromethylated alkyl ketones that are of great interest in medicinal chemistry. Preliminary mechanistic studies reveal that a bimetallic oxidative addition is likely involved in the reaction.