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.
雑誌名
Chemical Science
巻
11
号
31
ページ
8295 - 8300
発行年
2020-08-21
出版者
Royal Society of Chemistry
ISSN
20416520
EISSN
20416539
DOI
10.1039/D0SC02516J
権利
Open Access Article. Published on 21 July 2020. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
N- and O-arylation of pyridin-2-ones with diaryliodonium salts: base-dependent orthogonal selectivity under metal-free conditions
CheSci11_8295.pdf
(918.64KB)
NAOSITEについて