期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 48, 页码 25235-25240出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202108775
关键词
amination; lactams; photocatalysis; radical reactions
资金
- Institute for Basic Science in Korea [IBS-R10-D1]
- National Research Foundation of Korea (NRF) [NRF-2019H1A2A1076213]
- National Research Foundation of Korea [2019H1A2A1076213] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
In this study, an intramolecular C(sp(2))-H amidation of N-acyloxyamides under photoredox conditions was reported to produce delta-benzolactams with an aryl-alkyl sigma-bond relocation. Computational studies identified the N-[3,5-bis(trifluoromethyl)benzoyl] group as the most effective amidyl radical precursor, which led to the rationalization of radical-polar crossover for ring-expansion with C-C bond migration.
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.
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