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.
Highlights
Pyrrole is a very useful heterocyclic substrate to produce structural attributes of valuable chemicals, functional materials and pharmaceuticals [1,2,3,4,5]
Later in 2013, Xue and Xiao et al developed a method of photoredox catalysis in the presence of [Ru(bpy)3]2+ with visible light for the coupling reaction of arenes with unprotected or N-substituted pyrroles, pyrrole substrates were well tolerated with N-methyl and N-phenyl groups (Scheme 1a) [7]
Ackermann et al employed a 2,5-dimethylpyrrole derivative as substrate to deliver double arylated products at 3,4-positions of the pyrrole ring (Scheme 1b) [8]
Summary
Pyrrole is a very useful heterocyclic substrate to produce structural attributes of valuable chemicals, functional materials and pharmaceuticals [1,2,3,4,5]. Arylation of pyrrole derivatives with diaryliodonium salts for pyrrole–aryl coupling products is generating tremendous academic interest in organic synthesis. In 2012, the Zhang and Yu group reported that sodium hydroxide promoted direct arylation of unprotected pyrroles with diaryliodonium salts at the temperature of 80 °C, the coupling products were obtained in moderate to good yields (Scheme 1a) [6].
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