Open AccessHypervalent Iodine-based Trifluoromethylating Agents Made in Switzerland
Author(s) -
Nico Santschi,
Antonio Togni
Publication year - 2014
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2014.419
Subject(s) - hypervalent molecule , trifluoromethyl , reagent , iodine , chemistry , combinatorial chemistry , solid state , computational chemistry , organic chemistry , alkyl
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.