Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 14, Issue -, Pages 354-363Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.14.23
Keywords
benzyne; cycloaddition; diaryliodonium salts; N-phenylamine; pyrrole
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Funding
- National Nature Science Foundation of China (NSFC) [21472213, 21272069]
- National Key Program [2016YFA0200302]
- Fundamental Research Funds for the Central Universities
- Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
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With a strategy of the formation of benzynes by using diaryliodonium salts, a cycloaddition reaction of N-arylpyrroles with benzynes was reported. A wide range of bridge-ring amines with various substituents have been synthesized in moderate to excellent yields (35-96%). Furthermore, with a catalytic amount of TsOH center dot H2O, these amines can be converted into the corresponding N-phenylamine derivatives easily, which are potentially useful in photosensitive dyes.
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