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Selectfluor® Radical Dication (TEDA 2+. ) – A Versatile Species in Modern Synthetic Organic Chemistry
Author(s) -
Aguilar Troyano Francisco José,
Merkens Kay,
GómezSuárez Adrián
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000196
Subject(s) - chemistry , selectfluor , reactivity (psychology) , electron transfer , organic synthesis , halogen , dication , reagent , heteroatom , combinatorial chemistry , organic chemistry , molecule , alkyl , catalysis , medicine , alternative medicine , pathology
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.