Visible-Light Induced C(sp(2))-H Amidation with an Aryl-Alkyl sigma-Bond Relocation via Redox-Neutral Radical-Polar Crossover

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We report an approach for the intramolecular C(sp(2))-H amidation of N-acyloxyamides under photoredox conditions to produce delta-benzolactams with an aryl-alkyl sigma-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.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2021-11
Language
English
Article Type
Article
Citation

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.60, no.48, pp.25235 - 25240

ISSN
1433-7851
DOI
10.1002/anie.202108775
URI
http://hdl.handle.net/10203/289273
Appears in Collection
CH-Journal Papers(저널논문)
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