In:
Angewandte Chemie, Wiley, Vol. 132, No. 50 ( 2020-12-07), p. 22864-22872
Abstract:
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.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v132.50
DOI:
10.1002/ange.202010597
Language:
English
Publisher:
Wiley
Publication Date:
2020
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505868-5
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506609-8
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514305-6
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505872-7
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1479266-7
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505867-3
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506259-7
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