On the effect of backbone modifications in 3,3-dimethyl-1-(trifluoromethyl)-3H-1λ3,2-benziodaoxole

Article abstract of DOI:10.1002/ejoc.201403634

We report on the effect of small side-chain modifications to the structure of 3,3-dimethyl-1-(trifluoromethyl)-3H-1λ³,2-benziodaoxole (1b) on its reactivity, as expressed by the initial rate v₀ in a model reaction, and show how the latter can be successfully correlated to an easily determined physical parameter p, a ¹³C NMR chemical shift. The relationship v₀～ p is already present in the simplest starting material devoid of the hypervalent bond and the iodine core and, therefore, presents an interesting approach towards the future scaffold-optimization of this class of reagents. The reactivity of hypervalent-iodine-based trifluoromethylating agents, as expressed by the initial rate v₀ in a model reaction, correlates to an easily determined physical parameter p, a ¹³C NMR chemical shift.