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Diels-Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts.

ABSTRACT: 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·H2O, these amines can be converted into the corresponding N-phenylamine derivatives easily, which are potentially useful in photosensitive dyes.

SUBMITTER: Chen H

PROVIDER: S-EPMC5815300 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Diels-Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts.

Chen Huangguan H Han Jianwei J Wang Limin L

Beilstein journal of organic chemistry 20180206

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·H2O, these amines can be converted into the corresponding N-phenylamine derivatives easily, which are potentially useful in photosensitive dyes. ...[more]

PMID: 29507640

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