Organohypervalent Iodine: Development, Applications, and Future Directions

Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607, USA.
The Journal of Organic Chemistry (Impact Factor: 4.64). 05/2005; 70(8):2893-903. DOI: 10.1021/jo050117b
Source: PubMed

ABSTRACT The synthetic utility of organohypervalent iodine reagents will be illustrated by their use in the alpha-hydroxydimethylacetal formation reaction from enolizable ketones, alpha-hydroxylation, alpha-tosyloxylation, alpha-alkoxylation and arylation of ketones, carbon-carbon bond formation, and intramolecular cyclopropanation using iodonium ylides. The uses of these reagents in the Hunsdiecker reaction of carboxylic acids and Hofmann rearrangement of carboxamides is presented. Specific transformation in the cubane series are discussed. The syntheses of a wide range of heterocycle structures are also presented. A unifying pathway for virtually all these diverse reactions is offered; the central features being initial attack at the iodonium center, ligand coupling, with reductive elimination of iodobenzene to yield the product.