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Hydrogen-bond-assisted controlled C-H functionalization via adaptive recognition of a purine directing group Highly Cited Paper

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Title
Hydrogen-bond-assisted controlled C-H functionalization via adaptive recognition of a purine directing group
Author(s)
Hyun Jin Kim; Ajitha M.J.; Lee Y.; Ryu J.; Kim J.; Lee Y.; Jung Y.; Sukbok Chang
Publication Date
2014-01
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.136, no.3, pp.1132 - 1140
Publisher
AMER CHEMICAL SOC
Abstract
We have developed the Rh-catalyzed selective C-H functionalization of 6-arylpurines, in which the purine moiety directs the C-H bond activation of the aryl pendant. While the first C-H amination proceeds via the N1-chelation assistance, the subsequent second C-H bond activation takes advantage of an intramolecular hydrogen-bonding interaction between the initially formed amino group and one nitrogen atom, either N1 or N7, of the purinyl part. Isolation of a rhodacycle intermediate and the substrate variation studies suggest that N1 is the main active site for the C-H functionalization of both the first and second amination in 6-arylpurines, while N7 plays an essential role in controlling the degree of functionalization serving as an intramolecular hydrogen-bonding site in the second amination process. This pseudo-Curtin-Hammett situation was supported by density functional calculations, which suggest that the intramolecular hydrogen-bonding capability helps second amination by reducing the steric repulsion between the first installed ArNH and the directing group. © 2013 American Chemical Society.
URI
https://pr.ibs.re.kr/handle/8788114/1152
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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