Light-Mediated Formal Radical Deoxyfluorination of Tertiary Alcohols through Selective Single-Electron Oxidation with TEDA^2+.

ABSTRACT: 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®.

SUBMITTER: Aguilar Troyano FJ 

PROVIDER: S-EPMC6899844 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature