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Issue 14, 2018
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Carbene-catalyzed aerobic oxidation of isoquinolinium salts: efficient synthesis of isoquinolinones

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Abstract

A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.

Graphical abstract: Carbene-catalyzed aerobic oxidation of isoquinolinium salts: efficient synthesis of isoquinolinones

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Publication details

The article was received on 14 May 2018, accepted on 12 Jun 2018 and first published on 12 Jun 2018


Article type: Paper
DOI: 10.1039/C8GC01488D
Citation: Green Chem., 2018,20, 3302-3307
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    Carbene-catalyzed aerobic oxidation of isoquinolinium salts: efficient synthesis of isoquinolinones

    G. Wang, W. Hu, Z. Hu, Y. Zhang, W. Yao, L. Li, Z. Fu and W. Huang, Green Chem., 2018, 20, 3302
    DOI: 10.1039/C8GC01488D

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