Direct Addition of Grignard Reagents to Aliphatic Carboxylic Acids Enabled by Bulky turbo-Organomagnesium Anilides

The synthesis of ketones through addition of organometallic reagents to aliphatic carboxylic acids is a straightforward strategy that is limited to organolithium reagents. More desirable Grignard reagents can be activated and controlled with a bulky aniline-derived turbo-Hauser base. This operationally simple procedure allows the straightforward preparation of a variety of aliphatic and perfluoroalkyl ketones alike from functionalized alkyl, aryl and heteroaryl Grignard reagents.

Automated summary

The addition of organometallic reagents to aliphatic carboxylic acids for the synthesis of ketones is limited to organolithium reagents, but can be extended to Grignard reagents using a bulky aniline-derived turbo-Hauser base. This method allows for the straightforward preparation of a variety of aliphatic and perfluoroalkyl ketones.