Suzuki–Miyaura cross-coupling reaction on copper-trans-A2B corroles with excellent functional group tolerance

The palladium-catalyzed Suzuki–Miyaura cross-coupling reaction has been investigated on meso-substituted trans-A2B-corrole using tailored Pd-catalyst systems. We present the first examples of Suzuki–Miyaura cross-coupling reactions on meso-substituted trans-A2B-corrole derivatives with neutral, sterically hindered, inactivated and heteroaromatic boronic acids and esters, alkenylboronic acids, as well as quickly deboronating aryl boronic acids and benzo-condensated five membered heterocyclic boronic acids. In addition, we established a high-yield procedure for the Suzuki–Miyaura cross-coupling reaction of corroles with neutral boronic acids. Due to the lability of the free-base corrole macrocycles, functionalization of the corrole periphery was performed with the corresponding Cu-metallated species. meso-Substituted trans-A2B-corrole can hence be regarded as highly versatile platform towards more sophisticated corrole systems.