1.2 Deoxyfluorination of Aliphatic Alcohols

A. Joosten; J. Brioche

doi:10.1055/sos-SD-243-00001

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Paquin, J.-F. : 2024 Science of Synthesis, 2024/4: Modern Strategies in Organofluorine Chemistry 1 DOI: 10.1055/sos-SD-243-00001

Modern Strategies in Organofluorine Chemistry 1

1.2 Deoxyfluorination of Aliphatic Alcohols

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Editor: Paquin, J.-F.

Authors: Arimitsu, S. ; Barata-Vallejo, S. ; Brioche, J. ; Cahard, D. ; Charette, A. B. ; Chen, P. ; Crousse, B. ; De Borggraeve, W. M. ; Hu, M. ; Ismalaj, E. ; Joosten, A. ; Kordnezhadian, R. ; Lai, J. ; Liu, G. ; Luo, Y.-C. ; Peyrical, L. C. ; Postigo, A. ; Sammis, G. M. ; Shao, X. ; Shen, Q. ; Song, H.; Thomson, B. J. ; Wu, S.; Xu, C. ; Yerien, D. E. ; Zhang, X.

Title: Modern Strategies in Organofluorine Chemistry 1

Online ISBN: 9783132458253; Book DOI: 10.1055/b000000921

1st edition © 2024. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries

Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

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Abstract

The selective incorporation of fluoroalkyl motifs into complex organic molecules represents a significant challenge in fluorine chemistry. Among the various methods allowing the synthesis of alkyl fluorides, the deoxyfluorination of aliphatic alcohols remains one of the most practical, especially because substrates are readily available. This transformation has been popularized by the use of diethylaminosulfur trifluoride (DAST) and N,N-bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor) reagents. However, the safety and chemoselectivity issues related to these reagents have led to the development of innovative reagents and protocols to perform this key reaction. This review aims to highlight the recent progress made in the field of deoxyfluorination of aliphatic alcohols and to provide the reader with useful guidelines with a view to performing such a transformation.

Key words

organofluorine chemistry - deoxyfluorination - aliphatic alcohols - alkyl fluorides - nucleophilic fluorination (SN1 and SN2) - radical fluorination

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