Regioselective C-H Functionalization of HeteroareneN-Oxides Enabled by a Traceless Nucleophile

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Although N-alkenoxyheteroarenium salts have been widely used as umpoled synthons with nucleophilic (hetero)arenes, the use of electron-poor heteroarenes has remained unexplored. To overcome the inherent electron deficiency of quinolinium salts, a traceless nucleophile-triggered strategy was designed, wherein the quinolinium segment is converted into a dearomatized intermediate, thereby allowing simultaneous C8-functionalization of quinolines at room temperature. Experimental and computational studies support the traceless operation of a nucleophile, which enables the previously inaccessible transformation of N-alkenoxyheteroarenium salts. Remarkably, the generality of this strategy has been further demonstrated by broad applications in the regioselective C-H functionalization of other electron-deficient heteroarenes such as phenanthridine, isoquinoline, and pyridine N-oxides, offering a practical tool for the late-stage functionalization of complex biorelevant molecules.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2020-12
Language
English
Article Type
Article
Citation

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.59, no.50, pp.22675 - 22683

ISSN
1433-7851
DOI
10.1002/anie.202010597
URI
http://hdl.handle.net/10203/279172
Appears in Collection
CH-Journal Papers(저널논문)
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