Rh(III)-catalyzed C8 arylation of quinoline N-oxides with arylboronic acids

C8 aryl substituted of quinoline N-oxides were first obtained from a RhIII-catalyzed regioselective arylation of quinoline N-oxides with arylboronic acids as coupling partners. [Display omitted] Herein, we report the first RhIII-catalyzed regioselective C8 arylation of quinoline N-oxides with commer...

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Bibliographic Details
Published in:Chinese chemical letters 2020-06, Vol.31 (6), p.1572-1575
Main Authors: Huang, Yuanqiong, Lv, Xueli, Song, Hongjian, Liu, Yuxiu, Wang, Qingmin
Format: Article
Language:English
Subjects:
Arylboronic acids
C8 arylation
Quinoline N-oxides
Regioselectivity
RhIII-catalyzed
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Summary:C8 aryl substituted of quinoline N-oxides were first obtained from a RhIII-catalyzed regioselective arylation of quinoline N-oxides with arylboronic acids as coupling partners. [Display omitted] Herein, we report the first RhIII-catalyzed regioselective C8 arylation of quinoline N-oxides with commercially available arylboronic acids as coupling partners. This procedure is simple, and the reaction shows perfect regioselectivity, a broad substrate scope, and isolated yields of up to 92%. We demonstrate the utility of the reaction by using it for late-stage functionalization of a fungicide.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2019.11.028