Light-Mediated Formal Radical Deoxyfluorination of Tertiary Alcohols through Selective Single-Electron Oxidation with TEDA2+. |
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Authors: | Francisco José Aguilar Troyano Frederic Ballaschk Marcel Jaschinski Yasemin Özkaya Dr Adrián Gómez-Suárez |
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Institution: | 1. Organic Chemistry, Bergische Universität Wuppertal, Gaußstrasse 20, 42119 Wuppertal, Germany;2. Organic Chemistry, Bergische Universität Wuppertal, Gaußstrasse 20, 42119 Wuppertal, Germany
These authors contributed equally to this work. |
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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 TEDA2+. (TEDA: N-(chloromethyl)triethylenediamine), a radical cation derived from Selectfluor®. |
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Keywords: | fluorination mechanistic studies organic synthesis photochemistry radicals |
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