title: One-pot synthesis and applications of N-heteroaryl iodonium salts.
abstract: 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.
authors.affiliation: Department of Organic Chemistry, Stockholm University, 106 91 Stockholm (Sweden).
authors.forename: Marcin
authors.initials: M
authors.lastname: Bielawski
authors.affiliation: Department of Organic Chemistry, Stockholm University, 106 91 Stockholm (Sweden).
authors.forename: Joel
authors.initials: J
authors.lastname: Malmgren
authors.affiliation: Department of Organic Chemistry, Stockholm University, 106 91 Stockholm (Sweden).
authors.forename: Leticia M
authors.initials: LM
authors.lastname: Pardo
authors.affiliation: Department of Organic Chemistry, Stockholm University, 106 91 Stockholm (Sweden).
authors.forename: Ylva
authors.initials: Y
authors.lastname: Wikmark
authors.affiliation: Department of Organic Chemistry, Stockholm University, 106 91 Stockholm (Sweden).
authors.forename: Berit
authors.initials: B
authors.lastname: Olofsson
keywords: arylation; heterocycles; hypervalent iodine; iodonium salts; oxidation