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Light‐Mediated Formal Radical Deoxyfluorination of Tertiary Alcohols through Selective Single‐Electron Oxidation with TEDA 2+.
Author(s) -
Aguilar Troyano Francisco José,
Ballaschk Frederic,
Jaschinski Marcel,
Özkaya Yasemin,
GómezSuárez Adrián
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903702
Subject(s) - selectfluor , chemistry , tertiary alcohols , alkyl , alcohol , catalysis , organic chemistry , medicinal chemistry , photochemistry
The synthesis of tertiary alkyl fluorides through a formal radical deoxyfluorination process is described herein. This light‐mediated, catalyst‐free methodology is fast and broadly applicable allowing for the preparation of C−F bonds from (hetero)benzylic, propargylic, and non‐activated tertiary alcohol derivatives. Preliminary mechanistic studies support that the key step of the reaction is the single‐electron oxidation of cesium oxalates—which are readily available from the corresponding tertiary alcohols—with in situ generated TEDA 2+. (TEDA: N ‐(chloromethyl)triethylenediamine), a radical cation derived from Selectfluor®.