Organic Chemistry

Organohypervalent iodine reagents have attracted significant recent interest as versatile and environmentally benign oxidants and group transfer reagents with numerous applications in organic synthesis. One group of such compounds, the Togni reagents (CF3 lambda 3-iodanes) have been known since 2006 and are widely used as electrophilic trifluoromethylating reagents. The aim of this project is the synthesis and application of novel lambda 5-iodanes based on benziodoxole framework and featuring a fluoroalkyl group and an oxo group on the iodine atom. Preliminary study shows feasibility of the preparation of such compounds by oxidation of the Togni reagents. Determination of structure of these compounds and their reactivity in selective electrophilic fluoroalkylations and oxidations will be the objective of this investigation.

Key references
1. Charpentier J., Früh N., Togni A.: Chemical Reviews doi: 10.1021/cr500223h.
2. Zhdankin V. V.: Journal of Organic Chemistry 76: 1185-1197 (2011).