Journal of the American Chemical Society, Vol.140, No.32, 10140-10144, 2018
Functional Group Transposition: A Palladium-Catalyzed Metathesis of Ar-X sigma-Bonds and Acid Chloride Synthesis
We describe the development of a new method to use palladium catalysis to form functionalized aromatics: via the metathesis of covalent sigma-bonds between Ar-X fragments. This transformation demonstrates the dynamic nature of palladium-based oxidative addition/reductive elimination and offers a straightforward approach to incorporate reactive functional groups into aryl halides through exchange reactions. The reaction has been exploited to assemble acid chlorides without the use of high energy halogenating or toxic reagents and, instead, via the metathesis of aryl iodides with other acid chlorides.