Visible-Light-Photocatalyzed Synthesis of Phenanthridinones and Quinolinones via Direct Oxidative C-H Amidation

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A straightforward synthetic strategy to construct biologically relevant phenanthridinones and quinolinones was developed via visible-light-promoted direct oxidative C-H amidation. In this photocatalytic system, amidyl radicals can be generated by homolysis of the N-H bond of simple amide precursors via single-electron transfer under blue LED illumination, which leads to oxidative intramolecular C-H amidation. Moreover, an efficient synthetic strategy using a photocascade enabled facile assembly of quinolinone structures through a catalytic sequence involving triplet energy (E-T) transfer based E/Z olefin isomerization and subsequent photocatalytic generation of amidyl radical intermediates.
Publisher
AMER CHEMICAL SOC
Issue Date
2018-01
Language
English
Article Type
Article
Keywords

COUPLED ELECTRON-TRANSFER; ARYLATION REACTIONS; CASCADE REACTION; BOND ACTIVATION; ONE-POT; CATALYSIS; HETEROARENES; PHOTOREDOX; FUNCTIONALIZATION; AMINATION

Citation

ORGANIC LETTERS, v.20, no.1, pp.240 - 243

ISSN
1523-7060
DOI
10.1021/acs.orglett.7b03600
URI
http://hdl.handle.net/10203/240151
Appears in Collection
CH-Journal Papers(저널논문)
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