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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.

SUBMITTER: Bielawski M

PROVIDER: S-EPMC3943608 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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One-pot synthesis and applications of N-heteroaryl iodonium salts.

Bielawski Marcin M Malmgren Joel J Pardo Leticia M LM Wikmark Ylva Y Olofsson Berit B

ChemistryOpen 20140123 1

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 gro ...[more]

PMID: 24688890

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