Hypervalent Iodine-based Trifluoromethylating Agents Made in Switzerland

Authors

  • Nico Santschi Westfälische Wilhelms-Universität Münster Organisch-Chemisches Institut Corrensstrasse 40, D-48149 Münster, Germany. santschi@uni-muenster.de
  • Antonio Togni ETH Zürich Laboratory of Inorganic Chemistry Vladimir-Prelog-Weg 2 CH-8093 Zürich, Switzerland. togni@inorg.chem.ethz.ch

DOI:

https://doi.org/10.2533/chimia.2014.419

Keywords:

Electrophilic trifluoromethylation, Hypervalent iodine, Structure–reactivity relationship

Abstract

This account aims at providing a general overview over studies carried out in our group on 3,3-dimethyl-1-(trifluoromethyl)-3H-1?3,2-benziodaoxole (1) and 1-(trifluoromethyl)-3H-1?3,2-benziodaoxol-3-one (2). While the first part deals with the syntheses of these increasingly popular reagents, the second part provides in-depth analyses of solid state structures of different derivatives. By means of bond-length derived parameters p changes in the hypervalent bond resulting from backbone modifications could be classified. Furthermore, it is showcased that the parameter p also correlates to solution phase reactivities. Lastly, diverse strategies directed towards the activation of the reagents are exemplified based on selected applications of 1 and 2.

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Published

2014-06-26

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Scientific Articles