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N- and O-arylation of pyridin-2-ones with diaryliodonium salts: base-dependent orthogonal selectivity under metal-free conditions


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Title: N- and O-arylation of pyridin-2-ones with diaryliodonium salts: base-dependent orthogonal selectivity under metal-free conditions
Authors: Kuriyama, Masami / Hanazawa, Natsumi / Abe, Yusuke / Katagiri, Kotone / Ono, Shimpei / Yamamoto, Kosuke / Onomura, Osamu
Issue Date: 21-Aug-2020
Publisher: Royal Society of Chemistry
Citation: Chemical Science, 11(31), pp.8295-8300; 2020
Abstract: Metal-free N- and O-arylation reactions of pyridin-2-ones as ambident nucleophiles have been achieved with diaryliodonium salts on the basis of base-dependent chemoselectivity. In the presence of N,N-diethylaniline in fluorobenzene, pyridin-2-ones were very selectively converted to N-arylated products in high yields. On the other hand, the O-arylation reactions smoothly proceeded with the use of quinoline in chlorobenzene, leading to high yields and selectivities. In these methods, a variety of pyridin-2-ones in addition to pyridin-4-one and a set of diaryliodonium salts were accepted as suitable reaction partners.
URI: http://hdl.handle.net/10069/40266
ISSN: 20416520
DOI: 10.1039/D0SC02516J
Rights: Open Access Article. Published on 21 July 2020. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Type: Journal Article
Text Version: publisher
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/40266

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