2022
DOI: 10.1016/j.cclet.2021.09.067
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Visible-light-promoted radical alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester: Synthesis of oxazolines

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Cited by 20 publications
(12 citation statements)
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“…We envisioned that the activation of difluoro bromides under photocatalytic conditions could potentially generate the difluoroalkyl radical (RCF 2 • ), which would subsequently proceed through the tandem radical cyclization process with a molecule of oxygen to afford the target product. As part of our ongoing investigations on phototriggered C–H functionalization, herein we described a visible-light-mediated aerobic intramolecular cascade radical cyclization/hydroxylation of unactivated alkenes, providing novel and convenient access to the 4-hydroxyalkyl difluorinated-γ-lactams.…”
Section: Introductionmentioning
confidence: 99%
“…We envisioned that the activation of difluoro bromides under photocatalytic conditions could potentially generate the difluoroalkyl radical (RCF 2 • ), which would subsequently proceed through the tandem radical cyclization process with a molecule of oxygen to afford the target product. As part of our ongoing investigations on phototriggered C–H functionalization, herein we described a visible-light-mediated aerobic intramolecular cascade radical cyclization/hydroxylation of unactivated alkenes, providing novel and convenient access to the 4-hydroxyalkyl difluorinated-γ-lactams.…”
Section: Introductionmentioning
confidence: 99%
“…Carboxylic acids as starting materials are not only abundant, generally stable, and readily accessible in great structural diversity, and have also drawn much attention for their application as versatile radical precursors such as alkyl, aryl, carboxylic, and particularly acyl radicals (Mandal et al, 2018;Wang et al, 2019;Hu et al, 2020b;Chan et al, 2022;Kitcatt et al, 2022;Yan et al, 2022). Recently, an elegant strategy that combines photoredox catalysis and phosphoranyl radical-mediated deoxygenation makes it possible to form acyl radicals from carboxylic acids, providing streamlined access to structurally diverse ketones (Zhang et al, 2017;Stache et al, 2018).…”
Section: Introductionmentioning
confidence: 99%
“…However, a drawback of this procedure is that the organometallic reagents are not readily available. With our ongoing interest in developing green and efficient methods for C–H functionalization, herein, we report a novel and green photocatalysis approach for the synthesis of C-4 acylcoumarins via decarboxylative coupling reactions of α-keto acids and 3-nitrocoumarin in a redox-neutral fashion (Scheme c).…”
mentioning
confidence: 99%