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

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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… Click to show full abstract

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 α-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.

Keywords: aliphatic electrophiles; carbonylation secondary; arylboronic acids; catalyzed carbonylation; nickel catalyzed

Journal Title: ACS Catalysis
Year Published: 2019

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