Synthesis 2002(11): 1513-1518
DOI: 10.1055/s-2002-33339
PAPER
© Georg Thieme Verlag Stuttgart · New York

Progressive Direct Iodination of Sterically Hindered Alkyl Substituted
Benzenes

Stojan Stavber*, Petra Kralj, Marko Zupan
Laboratory for Organic and Bioorganic Chemistry, ‘Joef Stefan’ Institute and Department of Chemistry, University of Ljubljana, Jamova 39, 1000 Ljubljana, Slovenia
Fax: +386(61)4773811; e-Mail: stojan.stavber@ijs.si;
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Publikationsverlauf

Received 27 March 2002
Publikationsdatum:
23. August 2002 (online)

Abstract

Benzene derivatives bearing at least one bulky alkyl group (i-Pr or t-Bu) were selectively and effectively iodinated using elemental iodine activated by 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (SelectfluorTM, F-TEDA-BF4). Iodine atoms were progressively introduced at the most electron-rich and sterically less hindered position on the benzene ring. Not more than three iodine atoms could be progressively bonded to a target molecule bearing a i-Pr or t-Bu group.