Open AccessOne‐Pot Synthesis and Applications of N‐Heteroaryl Iodonium Salts
Author(s) -
Bielawski Marcin,
Malmgren Joel,
Pardo Leticia M.,
Wikmark Ylva,
Olofsson Berit
Publication year - 2014
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201300042
Subject(s) - moiety , nucleophile , chemoselectivity , chemistry , aryl , reactivity (psychology) , iodide , deprotonation , protonation , combinatorial chemistry , medicinal chemistry , organic chemistry , ion , catalysis , alkyl , medicine , alternative medicine , pathology
An efficient one‐pot synthesis of N‐heteroaryl iodonium triflates from the corresponding N‐heteroaryl iodide and arene has been developed. The reaction conditions resemble our previous one‐pot syntheses, with suitable modifications to allow N‐heteroaryl groups. The reaction time is only 30 min, and no anion exchange is required. The obtained iodonium salts were isolated in a protonated form, these salts can either be employed directly in applications or be deprotonated prior to use. The aryl groups were chosen to induce chemoselective transfer of the heteroaryl moiety to various nucleophiles. The reactivity and chemoselectivity of these iodonium salts were demonstrated by selectively introducing a pyridyl moiety onto both oxygen and carbon nucleophiles in good yields.