Suzuki-Miyaura cross-couplings from carboxylic acids via in situ acyl fluoride electrophiles

• Methodology developed allowing for Suzuki-Miyaura cross coupling to be carried out using carboxylic acids as ubiquitous starting materials to access high value ketones in a one-pot process. • In-situ activation approach allows use of carboxylic acids as starting materials which circumvents the need to use difficult to handle and costly isolated acyl fluoride electrophiles. • Reaction optimisation was conducted to establish reactivity in-line with isolated acyl fluorides. • A range of bi-aryl ketones were accessed in up to 92% yield in a one-pot two step procedure. Acyl fluorides have been previously shown to be competent electrophiles in the generation of ketones via Suzuki-Miyaura Cross-Couplings. However, such methodologies rely on isolated, pre-formed acyl fluorides which hampers the scope and flexibility of these approaches. In addition many acyl fluorides are unstable under ambient conditions and they suffer from instability during synthesis, isolation, or storage. Herein we report the use of an in situ generation of acyl fluorides in combination with Suzuki-Miyaura Cross-Coupling to generate di-aryl ketones. This allows the direct conversion of ubiquitous carboxylic acids to highly valuable ketones. The developed methodology was also found to be applicable to a range of aromatic and heteroaromatic carboxylic acids, affording an increased reaction scope compared to contemporary approaches.