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Selectfluor® Radical Dication (TEDA<sup>2+.</sup>) – A Versatile Species in Modern Synthetic Organic Chemistry

Francisco José Aguilar Troyano, Kay Merkens, Adrián Gómez‐Suárez

2020Asian Journal of Organic Chemistry76 citationsDOIOpen Access PDF

Abstract

Abstract Abstract : In radical processes involving Selectfluor®, 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®: 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.

Topics & Concepts

ChemistrySelectfluorReactivity (psychology)Electron transferOrganic synthesisHalogenDicationReagentHeteroatomCombinatorial chemistryOrganic chemistryMoleculeAlkylCatalysisMedicinePathologyAlternative medicineRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry
Selectfluor® Radical Dication (TEDA<sup>2+.</sup>) – A Versatile Species in Modern Synthetic Organic Chemistry | Litcius