Nickel-Catalyzed Mono-Selective α-Arylation of Acetone with Aryl Chlorides and Phenol Derivatives
Abderrahmane Amgoune and Anis Tlili show the α-arylation of acetone with aryl chlorides and phenol derivatives.
The development of straightforward methods for preparing α-arylated ketones directly from acetone is of great interest from both economic and synthetic points of view. While the arylation of carbonyl compounds with transition metal catalysts, via the formation of enolate intermediates, represents a powerful and relatively well-established class of carbon–carbon bond-forming reactions, the transposition of this technology to simple acetone has remained – in comparison – rather elusive. For example, this challenging transformation has rarely been achieved using palladium catalysis with aryl halide electrophiles. The transposition to more cost-effective nickel catalysts has proven highly challenging and the arylation of acetone had not been documented with nickel catalysts thus far (unlike some examples with other ketones).
This paper describes the results of a project that emerged from collaborative work between the group of Professor Abderrahmane Amgoune, colleagues Dr. Nuno Monteiro and Dr. Anis Tlili (all from Université de Lyon, France), and Dr. Johannes Schranck from Solvias AG (Switzerland).