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Synergistic Activation of Amides and Hydrocarbons for Direct C(sp3)–H Acylation Enabled by Metallaphotoredox Catalysis

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Title
Synergistic Activation of Amides and Hydrocarbons for Direct C(sp3)–H Acylation Enabled by Metallaphotoredox Catalysis
Author(s)
Geun Seok Lee; Joonghee Won; Seulhui Choi; Mu-Hyun Baik; Soon Hyeok Hong
Subject
acylation, ; amides, ; C−H activation, ; nickel, ; photocatalysis
Publication Date
2020-09
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.59, no.39, pp.16933 - 16942
Publisher
WILEY-V C H VERLAG GMBH
Abstract
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimThe utilizations of omnipresent, thermodynamically stable amides and aliphatic C(sp3)−H bonds for various functionalizations are ongoing challenges in catalysis. In particular, the direct coupling between the two functional groups has not been realized. Here, we report the synergistic activation of the two challenging bonds, the amide C−N and unactivated aliphatic C(sp3)−H, via metallaphotoredox catalysis to directly acylate aliphatic C−H bonds utilizing amides as stable and readily accessible acyl surrogates. N-acylsuccinimides served as efficient acyl reagents for the streamlined synthesis of synthetically useful ketones from simple C(sp3)−H substrates. Detailed mechanistic investigations using both computational and experimental mechanistic studies were performed to construct a detailed and complete catalytic cycle. The origin of the superior reactivity of the N-acylsuccinimides over other more reactive acyl sources such as acyl chlorides was found to be an uncommon reaction pathway which commences with C−H activation prior to oxidative addition of the acyl substrate
URI
https://pr.ibs.re.kr/handle/8788114/7659
DOI
10.1002/ange.202004441
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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