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분자활성 촉매반응 연구단
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Regioselective Introduction of Heteroatoms at the C-8 Position of Quinoline N-Oxides: Remote C-H Activation Using N-Oxide as a Stepping Stone Highly Cited Paper

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Title
Regioselective Introduction of Heteroatoms at the C-8 Position of Quinoline N-Oxides: Remote C-H Activation Using N-Oxide as a Stepping Stone
Author(s)
Heejun Hwang; Jinwoo Kim; Jisu Jeong; Sukbok Chang
Publication Date
2014-07
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.136, no.30, pp.10770 - 10776
Publisher
AMER CHEMICAL SOC
Abstract
Reported herein is the metal-catalyzed regioselective C-H functionalization of quinoline N-oxides at the 8-position: direct iodination and amidation were developed using rhodium and iridium catalytic systems, respectively. Mechanistic study of the amidation revealed that the unique regioselectivity is achieved through the smooth formation of N-oxide-chelated iridacycle and that an acid additive plays a key role in the rate-determining protodemetalation step. While this approach of remote C H activation using N-oxide as a directing group could readily be applied to a wide range of heterocyclic substrates under mild conditions with high functional group tolerance, an efficient synthesis of zinquin ester (a fluorescent zinc indicator) was demonstrated.
URI
https://pr.ibs.re.kr/handle/8788114/977
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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