Developing Novel Synthetic Methodologies Using Hypervalent Iodine(III) Reagents and Diazonium- or Iodonium Ylides

Abstract

Hypervalent iodine compounds have been established as useful reagents in synthetic chemistry due to their ease of handling and wide range of chemical reactivity under mild reaction conditions. Reported within are studies into the development of new methods for the gem-difunctionalization reactions using hypervalent iodine(III) compounds. Classic or modern hypervalent iodine reagents such as PhICl2, TolIF2, PhI(OAc)2, and 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-one were reacted with either a diazonium ylide or an iodonium ylide to facilitate gem-dichlorination, gem-difluorination, halogenative semi-pinacol, or cyclopropanation reactions. Oftentimes, catalytic amounts of additives served to activate the iodane and provide increased yields, faster reaction times, and higher chemoselectivity.