Journal
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
Volume 17, Issue 6, Pages 1347-1357Publisher
SPRINGER
DOI: 10.1007/s13738-020-01858-6
Keywords
Perfluoropyridine; Indole; Nucleophilic reaction; Heterocycle; Regioselectivity
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Funding
- Vali-e-Asr University of Rafsanjan
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The reaction of perfluoropyridines with indoles and bis(indolyl)methanes (BIMs) was investigated. The aromatic nucleophilic substitution of pentafluoropyridine with indoles occurs at the 4-position of pyridine ring by nitrogen site of indolyl anion, while reaction with 2,3,5,6-tetrafluoro-4-(phenylsulfonyl)pyridine gave a mixture of products arising substitution at 2-position of pyridine ring and replacement of phenylsulfonyl group. Furthermore, the reaction of pentafluoropyridine with BIMs yielded mixture of mono- and bis-perfluoropyridyl products. [GRAPHICS] .
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