1,2-Amidoarylcarbonylation of Styrenes to Access β‑Acylamino Ketones by NHC-Catalyzed Radical Relay

An amidoarylcarbonylation reaction of aromatic aldehydes and olefins with Katritzky pyridinium salts by N-heterocyclic carbene (NHC)-catalyzed radical relay to construct C–C and C–N bonds with good functional group tolerance is developed for the synthesis of β-acylamino ketones. This gentle and effi...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-09, Vol.89 (18), p.13085-13092
Main Authors: Yin, Dengyu, Lu, Lishuai, Jiang, Ying, Dou, Yandong, Fu, Ming-Chen, Zhu, Yanwu, Fan, Shilu
Format: Article
Language:English
Subjects:
carbenes
heterocyclic nitrogen compounds
organic chemistry
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Summary:An amidoarylcarbonylation reaction of aromatic aldehydes and olefins with Katritzky pyridinium salts by N-heterocyclic carbene (NHC)-catalyzed radical relay to construct C–C and C–N bonds with good functional group tolerance is developed for the synthesis of β-acylamino ketones. This gentle and efficient approach offers a valuable style for the synthesis of β-acylamino ketones. Mechanistic studies revealed that a radical addition/coupling/elimination cascade process was involved in this reaction.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01171