Скачать или смотреть Alcohols to Alkyl Fluorides, Part 3: Fluoroalkylamines

This presentation is about the conversion of aliphatic alcohols into alkyl fluorides by means of difluoroalkylamines as deoxyfluorinating reagents. These are slightly less reactive but more selective than aminosulfur trifluorides, and also quite easy to handle.
Fluoroalkylamines react with alcohols to yield first alkoxyiminium fluorides, which decompose into alkyl fluorides and amides. Thus, mechanistically these reagents are similar to the iminium chlorides used for the preparation of alkyl chlorides from alcohols. Neither acids nor bases are required, but due to the formation of hydrogen fluoride, the reaction mixtures should turn slightly acidic.
Alpha-Fluoroalkylamines are prepared by adding secondary amines to fluorinated olefins. These reactions proceed already at room temperature, and the resulting products show low basicity only, due to the strong electron-withdrawing effect of the fluoroalkyl group.

Further examples:

Org. Lett. 2016, 18, 6102-6104 (AlkylFluor);
Org. Proc. Res. Dev. 2014, 18, 1041-1044 (PhenoFluor);
Tetrahedron 2004, 60, 6923-6930 (Et2N-CF2-Ar);
Chem. Commun. 2002, 1618-1619 (PhenoFluor).

Reviews:
Org. Proc. Res. Dev. 2020, 24, 470-480;
Molecules 2017, 22, 977-1003 (application in heterocycle synthesis);
Synthesis 2017, 49, 4917-4930;
Org. Proc. Res. Dev. 2008, 12, 305-321.