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

2018; American Chemical Society; Volume: 83; Issue: 10 Linguagem: Inglês

10.1021/acs.joc.8b00730

1520-6904

Fei Ling, Chaowei Zhang, Chongren Ai, Yaping Lv, Weihui Zhong,

Bioactive Compounds and Antitumor Agents

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.