Formal Radical Deoxyfluorination of Oxalate‐Activated Alcohols Triggered by the Selectfluor‐DMAP Charge‐Transfer Complex

Author:

Baunis Haralds12,Pieber Bartholomäus12ORCID

Affiliation:

1. Department of Biomolecular Systems Max-Planck-Institute of Colloids and Interfaces Am Mühlenberg 1 14476 Potsdam Germany

2. Institute of Science and Technology Austria (ISTA) Am Campus 1 3400 Klosterneuburg Austria

Abstract

AbstractWe present a photon‐ and metal‐free approach for the radical fluorination of aliphatic oxalate‐activated alcohols. The method relies on the spontaneous generation of the N‐(chloromethyl)triethylenediamine radical dication, a potent single electron oxidant, from Selectfluor and 4‐(dimethylamino)pyridine. The protocol is easily scalable and provides the desired fluorinated products within only a few minutes reaction time.

Funder

Boehringer Ingelheim Stiftung

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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