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Palladium-Catalyzed Double-Isocyanide Insertion via Oxidative N–O Cleavage of Acetyl Oximes: Syntheses of 2H‑Pyrrol-2-imines

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posted on 16.02.2017, 15:21 by Gopal Chandru Senadi, Ting-Yi Lu, Ganesh Kumar Dhandabani, Jeh-Jeng Wang
The palladium-catalyzed reaction of acetyl oximes with isocyanides was developed for the synthesis of 2H-pyrrol-2-imines. The key steps were (i) generation of an enamido-palladium­(II) species, (ii) migratory double-isocyanide insertion, and (iii) cyclization. The scope of the synthesis of some 2H-pyrrol-2-imines was extended to the synthesis 1H-pyrrole-2,3-dione/1H-benzo­[g]­indole-2,3-dione derivatives via acid hydrolysis in a sequential one-pot manner.