Literature DB >> 32109331

Deoxyfluorination using CuF2 enabled by a Lewis base activating group strategy.

Deepali Eilidh Sood1, Sue Champion2, Daniel Dawson1, Sonia Chabbra1, Bela Bode1, Andrew Sutherland3, Allan J B Watson4.   

Abstract

Deoxyfluorination is a primary method for the formation of C-F bonds. Bespoke reagents are commonly used due to issues associated with the low reactivity of metal fluorides. Here, we report the development of a simple strategy for deoxyfluorination using first-row transition metal fluorides that overcomes these limitations. Using CuF 2 as an exemplar, activation of an O -alkylisourea adduct formed in situ allows effective nucleophilic fluoride transfer to a range of primary and secondary alcohols. Spectroscopic investigations have been used to probe the origin of the enhanced reactivity of CuF 2 . The utility of the process towards enabling 18 F-radiolabeling is also presented.
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Copper; PET; deoxyfluorination; fluorine; radiolabeling

Year:  2020        PMID: 32109331     DOI: 10.1002/anie.202001015

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  3 in total

Review 1.  Fluorine-18: Radiochemistry and Target-Specific PET Molecular Probes Design.

Authors:  Yunze Wang; Qingyu Lin; Hongcheng Shi; Dengfeng Cheng
Journal:  Front Chem       Date:  2022-06-29       Impact factor: 5.545

2.  Mechanochemical Nucleophilic Substitution of Alcohols via Isouronium Intermediates.

Authors:  Tatsiana Dalidovich; Jagadeesh Varma Nallaparaju; Tatsiana Shalima; Riina Aav; Dzmitry G Kananovich
Journal:  ChemSusChem       Date:  2022-01-20       Impact factor: 9.140

3.  Enantiospecific deoxyfluorination of cyclic α-OH-β-ketoesters.

Authors:  Christopher Mairhofer; Victoria Haider; Thomas Bögl; Mario Waser
Journal:  Org Biomol Chem       Date:  2021-01-06       Impact factor: 3.876

  3 in total

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