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

Huangguan Chen; Jianwei Han; Limin Wang

doi:10.3762/bjoc.14.23

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

Beilstein J Org Chem. 2018 Feb 6:14:354-363. doi: 10.3762/bjoc.14.23. eCollection 2018.

Authors

Huangguan Chen¹, Jianwei Han^{1

2}, Limin Wang¹

Affiliations

¹ Key Laboratory for Advanced Materials, Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
² Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

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.

Keywords: N-phenylamine; benzyne; cycloaddition; diaryliodonium salts; pyrrole.