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Gangadhar, Rao Mathi
분자활성 촉매반응 연구단
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Regioselective C-H Functionalization of HeteroareneN-Oxides Enabled by a Traceless Nucleophile

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Title
Regioselective C-H Functionalization of HeteroareneN-Oxides Enabled by a Traceless Nucleophile
Author(s)
Gangadhar Rao Mathi; Byeongseok Kweon; Yonghoon Moon; Yujin Jeong; Sungwoo Hong
Publication Date
2020-12
Journal
Angewandte Chemie - International Edition, v.59, no.50, pp.22675 - 22683
Publisher
John Wiley & Sons Ltd.
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
URI
https://pr.ibs.re.kr/handle/8788114/9314
DOI
10.1002/anie.202010597
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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