Iridium-catalysed arylation of C-H bonds enabled by oxidatively induced reductive elimination Highly Cited Paper

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Title
Iridium-catalysed arylation of C-H bonds enabled by oxidatively induced reductive elimination
Author(s)
Kwangmin Shin; Yoonsu Park; Mu-Hyun Baik; Sukbok Chang
Publication Date
2018-02
Journal
Nature Chemistry, v.10, no.2, pp.218 - 224
Publisher
NATURE PUBLISHING GROUP
Abstract
Direct arylation of C-H bonds is in principle a powerful way of preparing value-added molecules that contain carbon-aryl fragments. Unfortunately, currently available synthetic methods are not sufficiently effective to be practical alternatives to conventional cross-coupling reactions. We propose that the main problem lies in the late portion of the catalytic cycle where reductive elimination gives the desired carbon-aryl bond. Accordingly, we have developed a strategy where the Ir(III) centre of the key intermediate is first oxidized to Ir(IV). Density functional theory calculations indicate that the barrier to reductive elimination is reduced by nearly 19 kcal mol-1 for this oxidized complex compared with that of its Ir(III) counterpart. Various experiments confirm this prediction, affording a new methodology capable of directly arylating C-H bonds at room temperature with a broad substrate scope and in good yields. This work highlights how the oxidation states of intermediates can be targeted deliberately to catalyse an otherwise impossible reaction. ©2018 Macmillan Publishers Limited, part of Springer Nature. (c) All rights reserved
URI
https://pr.ibs.re.kr/handle/8788114/4651
ISSN
1755-4330
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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