Understanding and exploitation of neighboring heteroatom effect for the mild N-arylation of heterocycles with diaryliodonium salts under aqueous conditions: A theoretical and experimental mechanistic study

Tamás Bihari, Bence Babinszki, Zsombor Gonda, Szabolcs Kovács, Z. Novák, A. Stirling

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The mechanism of arylation of N-heterocycles with unsymmetric diaryliodonium salts is elucidated. The fast and efficient N-arylation reaction is interpreted in terms of the bifunctionality of the substrate: The consecutive actions of properly oriented Lewis base and Brønsted acid centers in sufficient proximity result in the fast and efficient N-arylation. The mechanistic picture points to a promising synthetic strategy where suitably positioned nucleophilic and acidic centers enable functionalization, and it is tested experimentally.

Original languageEnglish
Pages (from-to)5417-5422
Number of pages6
JournalJournal of Organic Chemistry
Issue number13
Publication statusPublished - Jul 1 2016


ASJC Scopus subject areas

  • Organic Chemistry

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