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Visible-Light Induced C(sp2)−H Amidation with an Aryl–Alkyl σ-Bond Relocation via Redox-Neutral Radical–Polar Crossover

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Title
Visible-Light Induced C(sp2)−H Amidation with an Aryl–Alkyl σ-Bond Relocation via Redox-Neutral Radical–Polar Crossover
Author(s)
Hyeyun Keum; Hoimin Jung; Jiwoo Jeong; Dongwook Kim; Sukbok Chang
Publication Date
2021-11-22
Journal
Angewandte Chemie - International Edition, v.60, no.48, pp.25235 - 25240
Publisher
John Wiley and Sons Inc
Abstract
© 2021 Wiley-VCH GmbH.We report an approach for the intramolecular C(sp2)−H amidation of N-acyloxyamides under photoredox conditions to produce δ-benzolactams with an aryl-alkyl σ-bond relocation. Computational studies on the designed reductive single electron transfer strategy led us to identify N-[3,5-bis(trifluoromethyl)benzoyl] group as the most effective amidyl radical precursor. Upon the formation of an azaspirocyclic radical intermediate by the selective ipso-addition with outcompeting an ortho-attack, radical–polar crossover was then rationalized to lead to the rearomative ring-expansion with preferential C−C bond migration.
URI
https://pr.ibs.re.kr/handle/8788114/10713
DOI
10.1002/anie.202108775
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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