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Synthesis of N-aryl amines enabled by photocatalytic dehydrogenation

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Title
Synthesis of N-aryl amines enabled by photocatalytic dehydrogenation
Author(s)
Kim, Jungwon; Siin Kim; Choi, Geunho; Lee, Geun Seok; Donghyeok Kim; Jungkweon Choi; Hyotcherl Ihee; Hong, Soon Hyeok
Publication Date
2021-02
Journal
CHEMICAL SCIENCE, v.12, no.5, pp.1915 - 1923
Publisher
ROYAL SOC CHEMISTRY
Abstract
Catalytic dehydrogenation (CD) via visible-light photoredox catalysis provides an efficient route for the synthesis of aromatic compounds. However, access to N-aryl amines, which are widely utilized synthetic moieties, via visible-light-induced CD remains a significant challenge, because of the difficulty in controlling the reactivity of amines under photocatalytic conditions. Here, the visible-light-induced photocatalytic synthesis of N-aryl amines was achieved by the CD of allylic amines. The unusual strategy using C6F5I as an hydrogen-atom acceptor enables the mild and controlled CD of amines bearing various functional groups and activated C-H bonds, suppressing side-reaction of the reactive N-aryl amine products. Thorough mechanistic studies suggest the involvement of single-electron and hydrogen-atom transfers in a well-defined order to provide a synergistic effect in the control of the reactivity. Notably, the back-electron transfer process prevents the desired product from further reacting under oxidative conditions.
URI
https://pr.ibs.re.kr/handle/8788114/9317
DOI
10.1039/d0sc04890a
ISSN
2041-6520
Appears in Collections:
Center for Nanomaterials and Chemical Reactions(나노물질 및 화학반응 연구단) > 1. Journal Papers (저널논문)
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