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1.
ChemistryOpen ; 3(1): 19-22, 2014 Feb.
Article in English | MEDLINE | ID: mdl-24688890

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.

3.
J Org Chem ; 73(12): 4602-7, 2008 Jun 20.
Article in English | MEDLINE | ID: mdl-18505294

ABSTRACT

Diaryliodonium salts have recently received considerable attention as mild arylation reagents in organic synthesis. This paper describes a regiospecific, sequential one-pot synthesis of symmetrical and unsymmetrical diaryliodonium tetrafluoroborates, which are the most popular salts in metal-catalyzed arylations. The protocol is fast and high-yielding and has a large substrate scope. Furthermore, the corresponding diaryliodonium triflates can conveniently be obtained via an in situ anion exchange.

4.
Chem Commun (Camb) ; (24): 2521-3, 2007 Jun 28.
Article in English | MEDLINE | ID: mdl-17563816

ABSTRACT

Unsymmetric and symmetric diaryliodonium triflates are synthesized from both electron-deficient and electron-rich substrates in a fast, high yielding, and operationally simple protocol employing arenes and aryl iodides or iodine.


Subject(s)
Biphenyl Compounds/chemical synthesis , Hydrocarbons, Iodinated/chemical synthesis , Iodine/chemistry , Mesylates/chemistry , Onium Compounds/chemical synthesis , Biphenyl Compounds/chemistry , Hydrocarbons, Iodinated/chemistry , Molecular Structure , Onium Compounds/chemistry
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