Directed C-H alkenylation of quinoline N-oxides at the C-8 position using a cationic rhodium(I) catalyst

Takanori Shibata; Yusuke Matsuo

doi:10.1002/adsc.201400223

Directed C-H alkenylation of quinoline N-oxides at the C-8 position using a cationic rhodium(I) catalyst

Takanori Shibata^*, Yusuke Matsuo

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

71 Citations (Scopus)

Abstract

The cationic rhodium-catalyzed alkenylation proceeds at the C-8 position of quinoline N-oxides. Regioselective C-H bond activation was achieved by the directing effect of the anionic oxygen of an N-oxide moiety, which can be readily removed by reductive treatment. A variety of 8-alkenylated quinoline N-oxides was obtained in moderate to high yields.

Original language	English
Pages (from-to)	1516-1520
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	356
Issue number	7
DOIs	https://doi.org/10.1002/adsc.201400223
Publication status	Published - 2014 May 5

Keywords

C-H activation
N-oxides
alkenylation
directing group
rhodium catalysts

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201400223

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abstract = "The cationic rhodium-catalyzed alkenylation proceeds at the C-8 position of quinoline N-oxides. Regioselective C-H bond activation was achieved by the directing effect of the anionic oxygen of an N-oxide moiety, which can be readily removed by reductive treatment. A variety of 8-alkenylated quinoline N-oxides was obtained in moderate to high yields.",

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AU - Matsuo, Yusuke

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N2 - The cationic rhodium-catalyzed alkenylation proceeds at the C-8 position of quinoline N-oxides. Regioselective C-H bond activation was achieved by the directing effect of the anionic oxygen of an N-oxide moiety, which can be readily removed by reductive treatment. A variety of 8-alkenylated quinoline N-oxides was obtained in moderate to high yields.

AB - The cationic rhodium-catalyzed alkenylation proceeds at the C-8 position of quinoline N-oxides. Regioselective C-H bond activation was achieved by the directing effect of the anionic oxygen of an N-oxide moiety, which can be readily removed by reductive treatment. A variety of 8-alkenylated quinoline N-oxides was obtained in moderate to high yields.

KW - C-H activation

KW - N-oxides

KW - alkenylation

KW - directing group

KW - rhodium catalysts

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Directed C-H alkenylation of quinoline N-oxides at the C-8 position using a cationic rhodium(I) catalyst

Abstract

Keywords

ASJC Scopus subject areas

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