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

Koóš, Peter

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

Posted on 2019-09-24 - 21:14

A unified catalytic system for tandem Pd-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.

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Čarný, Tomáš; Markovič, Martin; Gracza, Tibor; Koóš, Peter (2019). One-Step Synthesis of Isoindolo[2,1‑a]indol-6-ones via Tandem Pd-Catalyzed Aminocarbonylation and C–H Activation. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.9b02008

https://doi.org/10.1021/acs.joc.9b02008

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