Selectfluor® Radical Dication (TEDA2+.) - A Versatile Species in Modern Synthetic Organic Chemistry

: In radical processes involving Selectfluor (R), TEDA(2+.) (N-(chloromethyl)triethylenediamine) is often generated after an electron or fluorine transfer step. This is a highly reactive species that displays different and unique reactivity when compared to Selectfluor (R): It can act as a hydrogen atom transfer (HAT), halogen atom transfer (XAT), or aminating reagent, as well as a powerful single electron oxidant. Despite this versatility, the use of TEDA(2+.) in synthetic processes remains highly underexplored. This minireview, which covers recent applications of TEDA(2+.) to promote a wide range of C-heteroatom and C-C bond formations, aims to highlight the potential of this interesting species in organic chemistry. Particular attention is paid to mechanistic aspects involving how TEDA(2+.) is generated and the different reactivity patterns that it can display.