One-Step Synthesis of Isoindolo[2,1-a]indol-6-ones via Tandem Pd-Catalyzed Aminocarbonylation and C–H Activation

Tomáš Carny, Martin Markovic, Tibor Gracza and Peter KoošJ. Org. Chem. 2019, 84, 19, 12499–12507Publication Date:September 11, 2019

A unified catalytic system for tandem Palladium-catalyzed carbonylation and C–C cross-coupling via C–H activation was designed. The proposed cascade reaction allows a facile one-step construction of a tetracyclic isoindoloindole skeleton, in which three new C–C/C–N bonds are simultaneously formed. In detail, the carbonylation of aryl dibromides with indoles and C–H activation of in situ formed N-(2’-bromoaroyl)-indole provide biologically relevant 6H-isoindolo[2,1-a]indol-6-ones from commercially available substrates. The aminocarbonylation step in the proposed tandem reaction utilizes glyoxylic acid monohydrate as an environmentally friendly CO surrogate.