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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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
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Language:English
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carbenes
heterocyclic nitrogen compounds
organic chemistry
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container_issue 18
container_start_page 13085
container_title Journal of organic chemistry
container_volume 89
creator Yin, Dengyu
Lu, Lishuai
Jiang, Ying
Dou, Yandong
Fu, Ming-Chen
Zhu, Yanwu
Fan, Shilu
description 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.
doi_str_mv 10.1021/acs.joc.4c01171
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subjects carbenes
heterocyclic nitrogen compounds
organic chemistry
title 1,2-Amidoarylcarbonylation of Styrenes to Access β‑Acylamino Ketones by NHC-Catalyzed Radical Relay
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