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Metal-Oxidant-Free Cobalt-Catalyzed C(sp 2 )-H Carbonylation of ortho-Arylanilines: An Approach toward Free ( NH)-Phenanthridinones



Metal-Oxidant-Free Cobalt-Catalyzed C(sp 2 )-H Carbonylation of ortho-Arylanilines: An Approach toward Free ( NH)-Phenanthridinones



Journal of Organic Chemistry 83(10): 5698-5706



A traceless directing group assisted Co-catalyzed C(sp2)-H carbonylation of ortho-arylanilines for the synthesis of free ( NH)-phenanthridinones in metal-based-oxidant-free fashion was accomplished. This protocol employs diisopropyl azodicarboxylate as the CO source and oxygen as the sole oxidant, and provides good yields with various functional tolerance. The methodology has been applied for the total synthesis of PARP inhibitor PJ-34. Furthermore, the kinetic isotopic effect experiments reveal the C-H bond cleavage probably occurred in the rate-determining step.

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Accession: 065312659

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PMID: 29737168

DOI: 10.1021/acs.joc.8b00730


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