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

J Org Chem

Department of Organic Chemistry, Institute of Organic Chemistry, Catalysis and Petrochemistry , Slovak University of Technology, Radlinského 9 , SK-812 37 Bratislava , Slovakia.

Published: October 2019

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 -(2'-bromoaroyl)-indole provide biologically relevant 6-isoindolo[2,1-]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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http://dx.doi.org/10.1021/acs.joc.9b02008DOI Listing

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