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Zijun, Zhou
분자활성 촉매반응 연구단
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Photoinduced Transition-Metal-Free Chan-Evans-Lam-Type Coupling: Dual Photoexcitation Mode with Halide Anion Effect

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Title
Photoinduced Transition-Metal-Free Chan-Evans-Lam-Type Coupling: Dual Photoexcitation Mode with Halide Anion Effect
Author(s)
Zijun Zhou; Jeonguk Kweon; Hoimin Jung; Dongwook Kim; Sangwon Seo; Sukbok Chang
Publication Date
2022-05
Journal
Journal of the American Chemical Society, v.144, no.20, pp.9161 - 9171
Publisher
American Chemical Society
Abstract
© XXXX The Authors. Published by American Chemical Society.Herein, we report a photoinduced transition-metal-free C(aryl)-N bond formation between 2,4,6-tri(aryl)boroxines or arylboronic acids as an aryl source and 1,4,2-dioxazol-5-ones (dioxazolones) as an amide coupling partner. Chloride anion, either generated in situ by photodissociation of chlorinated solvent molecules or added separately as an additive, was found to play a critical cooperative role, thereby giving convenient access to a wide range of synthetically versatile N-arylamides under mild photo conditions. The synthetic virtue of this transition-metal-free Chan-Evans-Lam-type coupling was demonstrated by large-scale reactions, synthesis of 15N-labeled arylamides, and applicability toward biologically relevant compounds. On the basis of mechanistic investigations, two distinctive photoexcitations are proposed to function in the current process, in which the first excitation involving chloro-boron adduct facilitates the transition-metal-free activation of dioxazolones by single electron transfer (SET), and the second one enables the otherwise-inoperative 1,2-aryl migration of the thus-formed N-chloroamido-borate adduct.
URI
https://pr.ibs.re.kr/handle/8788114/11935
DOI
10.1021/jacs.2c03343
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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