Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 19, Pages 13720-13733Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01834
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Funding
- National Natural Science Foundation of China [22078084, 51874132]
- Scientific Research Fund of Hunan Provincial Education Department [20A224]
- Science and Technology Planning Project of Hunan Province [2020RC3056, 2018TP1017]
- Natural Science Foundation of Hunan Province [2020JJ5221, 2020JJ5212]
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The synthesis of 2-acyl-substituted 9H-pyrrolo[1,2-a]indoles was achieved through a visible-light-induced tandem acylation/cyclization of N-propargylindoles with aryl- or alkyl-substituted acyl oxime esters under transition-metal-free conditions, involving nitrogen-centered radical-mediated cleavage of the C-C a-bond in acyl oxime esters.
A convenient and efficient visible-light-induced tandem acylation/cyclization of N-propargylindoles with aryl- or alkyl-substituted acyl oxime esters for the synthesis of 2-acyl-substituted 9H-pyrrolo[1,2-a]indoles under transition-metal-free conditions, which proceeds via nitrogen-centered radical-mediated cleavage of the C-C a-bond in acyl oxime esters, is established. The aryl or alkyl acyl radicals, which come from acyl oxime esters, attack the C-C triple bonds in N-propargylindoles and then go through intramolecular cyclization/isomerization.
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