Light-Mediated Formal Radical Deoxyfluorination of Tertiary Alcohols through Selective Single-Electron Oxidation with TEDA2+.
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 TEDA2+. (TEDA: N-(chloromethyl)triethylenediamine), a radical cation derived from Selectfluor.
Aguilar Troyano, Francisco José,Ballaschk, Frederic,Jaschinski, Marcel,?zkaya, Yasemin,Gómez-Suárez, Adrián
supporting information
p. 14054 - 14058
(2019/11/11)
Molecular-modeling based design, synthesis, and activity of substituted piperidines as γ-secretase inhibitors
Alzheimer's disease (AD) is a debilitating disease widely thought to be associated with the accumulation of beta amyloid (Aβ) in the brain. Inhibition of γ-secretase, one of the enzymes responsible for Aβ production, may be a useful strategy for the treatment of AD. Described below is a series of γ-secretase inhibitors designed from a scaffold identified by a ROCS [J. Comput. Chem. 1996, 17, 1653] search of the corporate database.