期刊
GREEN CHEMISTRY
卷 20, 期 14, 页码 3302-3307出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8gc01488d
关键词
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资金
- National Key RAMP
- D Program of China [2017YFA0204704]
- National Key Basic Research Program of China (973) [2015CB932200]
- National Natural Science Foundation of China [21602105, 81672508, 61605074]
- Natural Science Foundation of Jiangsu Province [BK20171460, BK20140951]
- Jilin Province Key Laboratory of Organic Functional Molecular Design Synthesis [130028746]
- Postgraduate Research AMP
- Practice Innovation Program of Jiangsu Province [KYCX17_0959]
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.
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